Catalytic asymmetric hetero-Diels-Alder reactions of ketones: Chemzymatic reactions

Journal of the American Chemical Society

Volumn 120, Issue 34, 1998, Pages 8599-8605

  Yao, Sulan ^a   Johannsen, Mogens ^a   Audrain, Hélène ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032475445     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981710w     Document Type: Article

References (49)

1. See, e.g.: (a) Advances in Catalytic Processes: Asymmetric Chemical Transformations; Doyle, M., Ed.; JAI: Greenwich, CT, 1995; Vol. 1. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993. (c) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1995. (d) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley-Interscience: New York, 1993.
2. See, e.g.: (a) Advances in Catalytic Processes: Asymmetric Chemical Transformations; Doyle, M., Ed.; JAI: Greenwich, CT, 1995; Vol. 1. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993. (c) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1995. (d) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley-Interscience: New York, 1993.
3. See, e.g.: (a) Advances in Catalytic Processes: Asymmetric Chemical Transformations; Doyle, M., Ed.; JAI: Greenwich, CT, 1995; Vol. 1. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993. (c) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1995. (d) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley-Interscience: New York, 1993.
4. See, e.g.: (a) Advances in Catalytic Processes: Asymmetric Chemical Transformations; Doyle, M., Ed.; JAI: Greenwich, CT, 1995; Vol. 1. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Verlagsgesellschaft: Weinheim, 1993. (c) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1995. (d) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley-Interscience: New York, 1993.
5. Chemzyme, a specific molecule or complex which can catalyze a single chemical reaction for a particular chemical substrate with very high enantioselectivity and enantiospecificity at rates which approach "catalytic perfection". See, e.g.: Bugg, T. An Introduction to Enzyme and Coenzyme Chemistry; Blackwell Science: Oxford, 1997.
6. According to our knowledge, the term "chemzyme" has only been used very few times in relation to asymmetric catalysis. Two examples are the following: (a) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207. (b) Sasai, H.; Takayoshi, A.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. In the latter case, the word "chemzyme" was used only in the Introduction.
7. According to our knowledge, the term "chemzyme" has only been used very few times in relation to asymmetric catalysis. Two examples are the following: (a) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207. (b) Sasai, H.; Takayoshi, A.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. In the latter case, the word "chemzyme" was used only in the Introduction.
8. (a) See, e.g.: Boger, D. L.; Weinreb, S. N. In Hetero Diels - Alder Methodology in Organic Synthesis; Wasserman, H. H., Ed.; Academic Press: San Diego, CA, 1987; Vol. 47.
9. (b) Tietze, L. F.; Kettschau, G. Stereoselective Heterocyclic Synthesis I; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120.
10. (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
11. (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
12. (b) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 0, 5998.
13. (c) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979.
14. (d) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951.
15. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060 and references therein.
16. (f) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
17. (g) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757.
18. (h) Graven, A.; Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1996, 2372.
19. (a) Recently, we disclosed the enantioselective catalytic hetero-Diels-Alder reaction of ketones: Johannsen, M.; Yao, S.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1997, 2169.
20. (b) A previous attempt on asymmetric hetero-Diels-Alder reactions of ketones with chiral Lewis acids: Quimpère, M.; Jankowski, K. J. Chem. Soc., Chem. Commun. 1987, 676.
21. The Lewis acid- or chemzyme-catalyzed reactions should most adequately be considered as a kind of three-component coupling, as no covalent bonding between the substrates and catalyst occurs. This means that small catalyst loadings are very hard to obtain, and normal loadings are de facto in the range of 5-10 mol %. We are aware of one example of a chiral Lewis acid-catalyzed ene reaction where as little as 0.2 mol % of the Lewis acid was employed. However, only a single substrate was shown to react: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833.
22. For a review about the catalytic formation of molecules with quaternary carbon centers, see: Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 388.
23. For pioneering work using bisoxazolines and copper Lewis acids, see: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (b) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. (c) Evans, D. A.; Murry, J. A.; Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
24. For pioneering work using bisoxazolines and copper Lewis acids, see: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (b) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. (c) Evans, D. A.; Murry, J. A.; Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
25. For pioneering work using bisoxazolines and copper Lewis acids, see: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (b) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. (c) Evans, D. A.; Murry, J. A.; Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
26. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
27. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
28. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
29. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
30. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
31. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
32. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
33. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
34. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
35. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
36. For bisoxazoline-catalyzed asymmetric carbo-Diels - Alder reactions, see, e.g.: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. (b) Ishihara, K.; Corey, E. J. Tetrahedron Lett. 1992, 33, 6807. (c) Evans D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165. (f) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725. (h) Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145. (i) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454. (j) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1 and references therein.
37. (a) Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1997, 1183.
38. (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; Macmillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
39. For the particular effect of the bisoxazoline ligands on the absolute stereochemistry of the products, see, e.g.: Yao, S.; Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 2345 and references therein.
40. Mukaiyama, T.; Matsueda, R.; Suzuki, M. Tetrahedron Lett. 1970, 1901.
41. (a) Desimoni, G.; Faita, G.; Mella, M. Tetrahedron 1996, 52, 13649.
42. (b) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
43. (c) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
44. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
45. (e) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
46. (f) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
47. Weissberger, A.; Kibler, C. J. In Organic Syntheses; Horning, E. C., Ed.; John Wiley & Sons: New York, 1955; Collect. Vol. 3, pp 610-613.
48. (a) Myles, D. C.; Bigham, M. H. In Organic Syntheses; Meyers, A. I., Ed.; John Wiley & Sons: New York, 1992; Vol. 70, pp 231-239.
49. (b) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252.