Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3754-3760

  Vicario, Jose L ^a   Badía, Dolores ^a   Domínguez, Esther ^a   Rodríguez, Mónica ^a   Carrillo, Luisa ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHIRALITY; MOLECULAR INTERACTION; SPAIN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034674548     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000035h     Document Type: Article

References (135)

1. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317- 338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
2. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317- 338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
3. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317- 338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
4. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317-338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
5. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317- 338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
6. For some reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1, p 239. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-28. (d) Paterson, I. Contemp. Org. Synth. 1994, 1, 317- 338. (e) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. (e) Heathcock, C. H. Science 1981, 214, 395-401.
7. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995; Chapter 6, p 306.
8. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
9. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
10. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
11. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
12. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
13. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
14. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
15. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
16. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
17. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
18. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
19. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
20. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
21. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
22. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
23. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
24. For boron enolates, see: (a) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315. (b) Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-4724. (c) Masamune, S.; Sato, T.; Kim, B.-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (d) Reetz, M. T.; Rivaedeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 27, 3863-3866. (e) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977. (f) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173-5177. (g) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618-1621. (h) Abu Hena, M.; Terauchi, S.; Kim, C.-S.; Horiike, M.; Kiyooka, S.-I. Tetrahedron: Asymmetry 1998, 9, 1883-1890. For titanium enolates, see: (i) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. For tin enolates, see: (j) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252. For lithium enolates, see: (k) Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373-1377. (l) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620-1623. (m) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-338. (n) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969-4988. (o) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. (p) Landais, Y.; Ogay, P. Tetrahedron: Asymmetry 1994, 5, 541-544. (q) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
25. For recent reviews on catalytic asymmetric aldol reactions, see: (a) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
26. For recent reviews on catalytic asymmetric aldol reactions, see: (a) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137- 1141. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
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48. For a review, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. See also: (b) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807-5810. (c) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754-2760. (d) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 110, 9672- 9674. (e) Xiang, Y.; Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457-460. (f) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
49. For a review, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. See also: (b) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807-5810. (c) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754-2760. (d) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 110, 9672- 9674. (e) Xiang, Y.; Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457-460. (f) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
50. For a review, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. See also: (b) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807-5810. (c) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754-2760. (d) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 110, 9672-9674. (e) Xiang, Y.; Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457-460. (f) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
51. For a review, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. See also: (b) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807-5810. (c) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754-2760. (d) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 110, 9672- 9674. (e) Xiang, Y.; Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457-460. (f) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
52. For a review, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. See also: (b) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807-5810. (c) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754-2760. (d) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 110, 9672- 9674. (e) Xiang, Y.; Olivier, E.; Ouimet, N. Tetrahedron Lett. 1992, 33, 457-460. (f) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
53. Tanner, D.; Bigerson, C.; Gogoll, A. Tetrahedron 1994, 50, 9797-9824.
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67. See, for example: (a) Carrillo, L.; Badía, D.; Domínguez, E.; Vicario, J. L.; Tellitu, I. J. Org. Chem. 1997, 62, 6716-6721. (b) Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. J. Org. Chem. 1999, 64, 4610-4616.
68. See, for example: (a) Carrillo, L.; Badía, D.; Domínguez, E.; Vicario, J. L.; Tellitu, I. J. Org. Chem. 1997, 62, 6716-6721. (b) Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. J. Org. Chem. 1999, 64, 4610-4616.
69. Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. Tetrahedron Lett. 1998, 39, 9267-9270.
70. For the use of (S,S)-(+)-pseudoephedrine as chiral auxiliary, see: (a) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (b) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
71. For the use of (S,S)-(+)-pseudoephedrine as chiral auxiliary, see: (a) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (b) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
72. For the use of (S,S)-(+)-pseudoephedrine as chiral auxiliary, see: (a) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (b) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
73. The isomers ent-2a and ent-3a were obtained as pure compounds by epimerizing the α-carbon of 3a and 2a, respectively, with LDA in refluxing THF followed by column chomatography separation of the two formed diastereoisomers (3a and ent-Za in the reaction of 3a and 2a and ent-3a in the reaction of 2a).
74. For the effect of LiCl in the reaction of pseudoephedrine amide enolates, see: Rück, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433-435. See also: Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339-1347 and references therein.
75. For the effect of LiCl in the reaction of pseudoephedrine amide enolates, see: Rück, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433- 435. See also: Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339-1347 and references therein.
76. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
77. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
78. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
79. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009-6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
80. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
81. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
82. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
83. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
84. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
85. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
86. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
87. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
88. For some representative examples of aldol reactions with a previous transmetalation step, see: (a) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975-3978. (b) Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett. 1983, 24, 5233-5236. (c) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343-3346. (d) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26, 6009- 6012. (e) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217-2220. (f) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900. (g) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 457-460. (h) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. (i) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498. (j) Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J. Org. Chem. 1991, 56, 5978-5980. (k) van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499- 2506. (l) Hayashi, T. Tetrahedron Lett. 1991, 32, 5369-5372. (m) Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 8245-9248. See also refs 6c, 9a, 10b, 13, 14, and 16.
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90. For computer modeling calculations supporting this pseudochair intermediate, see: (a) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303. (b) Leung-Toung, R.; Tidwell, T. T. J. Am. Chem. Soc. 1990, 112, 1042-1048. (c) Li, Y.; Paddon-Row: N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 1613-1636.
91. For computer modeling calculations supporting this pseudochair intermediate, see: (a) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303. (b) Leung-Toung, R.; Tidwell, T. T. J. Am. Chem. Soc. 1990, 112, 1042-1048. (c) Li, Y.; Paddon-Row: N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 1613-1636.
92. For computer modeling calculations supporting this pseudochair intermediate, see: (a) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303. (b) Leung-Toung, R.; Tidwell, T. T. J. Am. Chem. Soc. 1990, 112, 1042-1048. (c) Li, Y.; Paddon-Row: N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 1613-1636.
93. For computer modeling calculations supporting this pseudochair intermediate, see: (a) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303. (b) Leung-Toung, R.; Tidwell, T. T. J. Am. Chem. Soc. 1990, 112, 1042-1048. (c) Li, Y.; Paddon-Row: N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 1613-1636.
94. (a) Phillips, J. K.; Miller, S. P. F.; Andersen, J. F.; Fales, H. M.; Burkholder, W. E. Tetrahedron Lett. 1987, 28, 6145-6146.
95. (b) Philips, J. K.; Chong, J. M.; Andersen, J. F.; Burkholder, W. E. Entomol. Exp. Appl. 1989, 51, 149-155.
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99. (b) Walgenbach, C. A.; Phillips, J. K.; Burkholder, W. E.; King, G. G. S.; Slessor, K. N.; Mori, K. J. Chem. Ecol. 1987, 13, 2159-2166.
100. (a) Omura, S.; Tanaka, H. In Macrolide Antibiotics: Chemistry, Biology, Practice; Omura, S., Ed.; Academic Press: New York, 1984; p 351.
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102. For a review on the synthesis of 1,3-polyol chains, see: (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040. (b) Oishi, T.; Nakata, T. Synthesis 1990, 635-645.
103. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
104. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
105. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
106. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
107. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
108. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
109. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
110. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
111. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
112. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
113. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
114. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
115. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
116. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
117. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
118. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
119. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
120. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
121. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
122. For 1,3-syn reduction of β-hydroxy ketones, see: (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (b) Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, J. M. H. Tetrahedron Lett. 1985, 26, 2951-2954. (c) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1985, 28, 155-158. (d) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (e) Bonadies, F.; Di Fabio, R.; Gubbioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703- 706. (f) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467- 6470. (g) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (h) Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192. (i) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (j) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050. (k) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (l) Yamashita, H.; Narasaka, K. Chem. Lett. 1996, 539-543. (m) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841-5844. For 1,3-anti reduction, see: (n) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276. (o) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-12. (p) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560- 3578. (q) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (r) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447- 6449. (s) Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409-3412. (t) Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705-7708.
123. (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
124. (b) Hoveyda, A.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
125. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338-345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
126. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
127. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
128. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
129. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
130. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
131. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
132. For some examples of reduction of α-alkyl substituted β-hydroxy ketones, see: (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338- 345. (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-I. Tetrahedron Lett. 1986, 27, 6233-6237. (c) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866- 868. (e) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173-176. (f) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868-873. (g) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089. (h) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Mercantoni, E.; Sambri, L. Tetrahedron Lett. 1999, 40, 2845-2848.
133. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199-2204.
134. Cram, D. J.; Kopecki, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755.
135. For general experimental procedures, see ref 21b.