Direct catalytic asymmetric aldol reaction

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4168-4178

  Yoshikawa, Naoki ^a   Yamada, Yoichi M A ^a   Das, Jagattaran ^a   Sasai, Hiroaki ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONCENTRATION RESPONSE; DIASTEREOISOMER; ENANTIOMER; PROTON TRANSPORT; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0033526380     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990031y     Document Type: Article

References (92)

1. For some reviews, see: (a) Kim, B. M.; Williams, S. F.; Masamune, S. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1.7, p 239. (b) Heathcock, C. H. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, part B, p 111.
2. For some reviews, see: (a) Kim, B. M.; Williams, S. F.; Masamune, S. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2 (Heathcock, C. H., Ed.), Chapter 1.7, p 239. (b) Heathcock, C. H. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, part B, p 111.
3. (a) Liu, J.-F.; Abiko, A.; Pei, Z.; Buske, D. C.; Masamune, S. Tetrahedron Lett. 1998, 39, 1873-1876.
4. (b) Wang, Y.-C.; Hung, A.-W.; Chang, C.-S.; Yan, T.-H. J. Org. Chem. 1996, 61, 2038-2043.
5. (c) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613-2636.
6. (d) Otsuka, K.; Ishizuka, T.; Kimura, K.; Kunieda, T. Chem. Pharm. Bull. 1994, 42, 748-750.
7. (e) Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321-4324.
8. (f) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290.
9. (g) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750.
10. (h) Reetz, M. T.; Rivadeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 31, 3863-3866.
11. (i) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315.
12. (j) Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
13. (k) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129 and references therein.
14. (a) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 8, 2527-2528.
15. (b) Palomo, C.; Oiarbide, M.; González, A.; García, J. M.; Berrée, F.; Linden, A. Tetrahedron Lett, 1996, 37, 6931-6934.
16. (c) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.; Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306.
17. (d) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498.
18. (e) Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299-1308.
19. (f) Duthaler, R. O.; Herold, P.; Wyler-Helfer, S.; Riediker, M. Helv. Chim. Acta 1990, 73, 659-673 and references therein.
20. (a) Mukaiyama, T.; Shiina, I.; Uchiro, H.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1994, 67, 1708-1716.
21. (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442.
22. (c) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672-9674.
23. (d) Gennari, C.; Bernardi, A.; Colombo, L.; Scolastico, C. J. Am. Chem. Soc. 1985, 107, 5812-5813.
24. (e) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875 and references therein.
25. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
26. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
27. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
28. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
29. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
30. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441-1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
31. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
32. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
33. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
34. For Zr enolates, see: (a) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318-1320. (b) Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876-2878 and references therein. For Sn enolates, see: (c) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772. (d) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217-1220. (e) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761. (f) Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1982, 1441- 1444, and references therein. For Li enolates, see: (g) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. (h) Muraoka, M.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1988, 29, 337-339 and references therein. See also: refs 3b and 5c. For other enolates, see: (i) Powers, T. S.; Kenneth, Y. S.; Wilson, K. J.; Wulff, W. D. J. Org. Chem. 1994, 59, 6882-6884. (j) Davies, S. G.; Dordor-Hedgecock, I. M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125-2128 and references therein.
35. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
36. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
37. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
38. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
39. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
40. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
41. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
42. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
43. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
44. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
45. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
46. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
47. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
48. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
49. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
50. For recent examples of catalytic asymmetric Mukaiyama-aldol reactions, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (b) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838. (c) Chen, C.- T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341-11342. (d) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (e) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334. (f) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466. (g) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71-74. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364. (i) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. (j) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772. (k) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910. (l) Kiyooka, S.-I.; Kaneko, Y.; Kume, K.-I. Tetrahedron Lett. 1992, 33, 4927-4930. (m) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732. (n) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042 and references therein. For some reviews, see: (o) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (p) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137-1141.
51. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
52. (b) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis; Ojima, I., Ed; VCH: New York, 1993, pp 367-388.
53. (a) Fessner, W.-D.; Schneider, A.; Held, H.; Sinerius, G.; Walter, C.; Hixon, M.; Schloss, J. V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2219-2221 and references therein.
54. For catalytic asymmetric aldol reactions using catalytic antibodies, see: (b) Zhong, G.; Shabat, D.; List, B.; Anderson, J.; Sinha, S. C.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1998, 37, 2481-2484 and references therein.
55. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
56. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
57. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
58. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
59. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
60. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
61. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
62. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
63. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
64. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
65. For a review, see: (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl, 1997, 36, 1236-1256. For each reaction, see: (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (c) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368-1372. (d) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656- 6657. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373. (f) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (g) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044. (h) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H,-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223-2226. (j) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103. (k) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
66. For an excellent review, see: Steinhagen, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2339-2342.
67. A partially successful attempt to develop a direct catalytic asymmetric aldol reaction has been reported; however, only one reactive aldehyde and acetone were used, and the ee of the corresponding product was not determined. See: Nakagawa, M.; Nakao, H.; Watanabe, K.-I. Chem. Lett. 1985, 391-394.
68. The enantiomeric excesses of all of the aldol adducts were determined by HPLC analysis using DAICEL CHIRALPAK AS, AD, CHIRALCEL OJ or OD. The absolute configurations of 3k, 3m, and 3o were determined to be (S)-form and that of 31 to be (R)-form by the Mosher's method. See: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. The absolute configuration of 3n was determined to be (R)-form by relation to 3m. For other adducts, see refs 20a, c and references therein.
69. 2O in THF (1.0 M) to give hydrated (R)-LLB. This had been found to be a more effective catalyst for previously reported catalytic asymmetric nitroaldol reactions. See ref 9c.
70. Results using 5 or 10 mol % of (R)-LLB: 42% yield, 77% ee; 52% yield, 88% ee, respectively.
71. 2 (33%, 15% ee), LnLB where Ln = Pr, Sm, Gd, Dy, or Yb in THF (low ee's), LLB* in THF (B* = 6,6′-bis-((triethylsilyl)ethynyl)(binaphthoxide) (low ee), 6,6′-dibromo(binaphthoxide) (low ee), 6,6′-dimethoxy(binaphthoxide) (low ee)).
72. The moderate yield is mainly due to the low reactivity of LLB. A small amount of dehydrated product was detected.
73. The self-condensation of the aldehyde can be suppressed at low temperature (-40°C) using 3′-nitroacetophenone (see Table 4, entry 11).
74. A trace amount of 4-hydroxy-3,5,5-trimethyl-6-phenyl-2-hexanone was detected.
75. 3-tris((R)-binaphthoxide) ((R)-YbLB), the same reaction conditions gave the aldol product with 36% ee (R) and 47% yield.
76. The result was reported previously, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) C&EN News 1997, September 8, 30. We have also succeeded in developing the direct asymmetric aldol reaction utilizing the first asymmetric barium catalyst. See: (c) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561-5564.
77. The result was reported previously, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) C&EN News 1997, September 8, 30. We have also succeeded in developing the direct asymmetric aldol reaction utilizing the first asymmetric barium catalyst. See: (c) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561-5564.
78. The result was reported previously, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) C&EN News 1997, September 8, 30. We have also succeeded in developing the direct asymmetric aldol reaction utilizing the first asymmetric barium catalyst. See: (c) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561-5564.
79. Aldehyde 1i was synthesized as follows: (equation presented)
80. (R)-Catalyst has also been found to promote the aldol reaction with negligible racemization of aldehyde 1i as well.
81. Aldehyde 1j was synthesized as follows: (a) Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346-4348. (b) Hutchins, R. O.; Kandasamy, D.; Dux, F., III; Maryanoff, C. A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro J.; Puglis, J. J. Org. Chem. 1978, 43, 2259-2267. (equation presented)
82. Aldehyde 1j was synthesized as follows: (a) Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346- 4348. (b) Hutchins, R. O.; Kandasamy, D.; Dux, F., III; Maryanoff, C. A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro J.; Puglis, J. J. Org. Chem. 1978, 43, 2259-2267. (equation presented)
83. 4. Furthermore, the ee of this aldehyde was determined to be more than 92% on the basis of analyses of the corresponding aldol products.
84. 1H NMR analysis of the crude product. The relative configuration of syn -3o was determined by X-ray crystallographic analysis.
85. Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 523-524.
86. Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407-7408.
87. Göttlich, R.; Yamakoshi, K.; Sasai, H.; Shibasaki, M. Synlett 1997, 971-973.
88. In usual aldol reactions, the rate is known to be proportional to the concentration of the aldehyde. See: (a) Coombs, E.; Evans, D. P. J. Chem. Soc. 1940, 1295-1300. (b) Noyce, D. S.; Pryor, W. A. J. Am. Chem. Soc. 1955, 77, 1397-1401. (c) Noyce, D. S.; Pryor, W. A.; Bottini, A. H. J. Am. Chem. Soc. 1955, 77, 1402-1405.
89. In usual aldol reactions, the rate is known to be proportional to the concentration of the aldehyde. See: (a) Coombs, E.; Evans, D. P. J. Chem. Soc. 1940, 1295-1300. (b) Noyce, D. S.; Pryor, W. A. J. Am. Chem. Soc. 1955, 77, 1397-1401. (c) Noyce, D. S.; Pryor, W. A.; Bottini, A. H. J. Am. Chem. Soc. 1955, 77, 1402-1405.
90. In usual aldol reactions, the rate is known to be proportional to the concentration of the aldehyde. See: (a) Coombs, E.; Evans, D. P. J. Chem. Soc. 1940, 1295-1300. (b) Noyce, D. S.; Pryor, W. A. J. Am. Chem. Soc. 1955, 77, 1397-1401. (c) Noyce, D. S.; Pryor, W. A.; Bottini, A. H. J. Am. Chem. Soc. 1955, 77, 1402-1405.
91. For a review, see: Cockerill, A. F.; Davies, G. L. O.; Harden, R. C.; Rackham, D. M. Chem. Rev. 1913, 73, 553-588 and references therein.
92. It is unlikely, even if the aldehyde coordinates to a Li-atom of the Pr complex, that either the proximity to the Pr or alternatively the positioning of the formyl C-H in the shielding region of the naphthyl ring could produce a shift of such magnitude, since no such chemical shift is observed in the presence of LLB.