Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine - Copper catalyst [14]

Journal of the American Chemical Society

Volumn 121, Issue 40, 1999, Pages 9473-9474

  Appella, Daniel H ^a   Moritani, Yasunori ^a   Shintani, Ryo ^a   Ferreira, Eric M ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA METHYLCINNAMIC ACID ETHYL ESTER; COPPER; COPPER CHLORIDE; ESTER DERIVATIVE; PHOSPHINE; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; LETTER; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY;

EID: 0033552259     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992366l     Document Type: Letter

References (54)

1. (a) Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 7649.
2. (b) Keller, E.; Maurer, J.; Naasz, R.; Schader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998 9, 2409.
3. (c) Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron 1998, 54, 10295.
4. (d) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
5. (e) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11.
6. (f) Krause, N. Angew. Chem., Int, Ed. 1998, 37, 283 and references therein.
7. (a) Asymmetric hydrogenations that generate a chiral center β to a carbonyl: Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319. Saburi, M.; Takeuchi, H.; Ogasawara, M.; Tsukahara, T.; Ishii, Y.; Ikariya, T.; Takahashi, T.; Uchida, Y. J. Organomet. Chem. 1992, 428, 155. Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510. Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 7, 2897.
8. (a) Asymmetric hydrogenations that generate a chiral center β to a carbonyl: Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319. Saburi, M.; Takeuchi, H.; Ogasawara, M.; Tsukahara, T.; Ishii, Y.; Ikariya, T.; Takahashi, T.; Uchida, Y. J. Organomet. Chem. 1992, 428, 155. Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510. Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 7, 2897.
9. (a) Asymmetric hydrogenations that generate a chiral center β to a carbonyl: Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319. Saburi, M.; Takeuchi, H.; Ogasawara, M.; Tsukahara, T.; Ishii, Y.; Ikariya, T.; Takahashi, T.; Uchida, Y. J. Organomet. Chem. 1992, 428, 155. Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510. Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 7, 2897.
10. (a) Asymmetric hydrogenations that generate a chiral center β to a carbonyl: Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319. Saburi, M.; Takeuchi, H.; Ogasawara, M.; Tsukahara, T.; Ishii, Y.; Ikariya, T.; Takahashi, T.; Uchida, Y. J. Organomet. Chem. 1992, 428, 155. Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510. Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 7, 2897.
11. (a) Asymmetric hydrogenations that generate a chiral center β to a carbonyl: Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319. Saburi, M.; Takeuchi, H.; Ogasawara, M.; Tsukahara, T.; Ishii, Y.; Ikariya, T.; Takahashi, T.; Uchida, Y. J. Organomet. Chem. 1992, 428, 155. Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510. Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 7, 2897.
12. (b) Asymmetric hydrogenations that simutaneously generate chiral centers a and β to a carbonyl: Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876. Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
13. (b) Asymmetric hydrogenations that simutaneously generate chiral centers a and β to a carbonyl: Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876. Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
14. (b) Asymmetric hydrogenations that simutaneously generate chiral centers a and β to a carbonyl: Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876. Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
15. (b) Asymmetric hydrogenations that simutaneously generate chiral centers a and β to a carbonyl: Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876. Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
16. Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1975, 3.
17. (a) Cu catalysts: Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180. Tsuda, T.; Yoshida, T.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1987, 52, 1624. Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887.
18. (a) Cu catalysts: Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180. Tsuda, T.; Yoshida, T.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1987, 52, 1624. Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887.
19. (a) Cu catalysts: Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180. Tsuda, T.; Yoshida, T.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1987, 52, 1624. Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887.
20. (b) Ir catalyst: Apple, D. C.; Brady, K. A.; Chance, J. M.; Heard, N. E.; Nile, T. A. J. Mol. Catal. 1985, 29, 55.
21. (c) Mo catalysts: Keinan, E.; Perez, D. J. Org. Chem. 1987, 52, 2576. Schmidt, T. Tetrahedron Lett. 1994, 35, 3513.
22. (c) Mo catalysts: Keinan, E.; Perez, D. J. Org. Chem. 1987, 52, 2576. Schmidt, T. Tetrahedron Lett. 1994, 35, 3513.
23. Ni catalysts: Caporusso, A. M.; Giacomelli, G.; Lardicci, L. J. Org. Chem. 1982, 47, 4640. Boudjouk, P.; Choi, S.,-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951.
24. Ni catalysts: Caporusso, A. M.; Giacomelli, G.; Lardicci, L. J. Org. Chem. 1982, 47, 4640. Boudjouk, P.; Choi, S.,-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951.
25. (e) Pd catalysts: Keinan, E.; Greenspoon, N. J. Am. Chem. Soc. 1986, 108, 7314. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Synlett 1991, 27.
26. (e) Pd catalysts: Keinan, E.; Greenspoon, N. J. Am. Chem. Soc. 1986, 108, 7314. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Synlett 1991, 27.
27. (f) Pt catalysts: Barlow, A. P.; Boag, N. M.; Stone, F. G. A. J. Organomet. Chem. 1980, 191, 39. Johnson, C. R.; Raheja, R. K. J. Org. Chem. 1994, 59, 2287.
28. (f) Pt catalysts: Barlow, A. P.; Boag, N. M.; Stone, F. G. A. J. Organomet. Chem. 1980, 191, 39. Johnson, C. R.; Raheja, R. K. J. Org. Chem. 1994, 59, 2287.
29. (g) Rh catalysts: Yoshii, E.; Kobayashi, Y.; Koizumi, T.; Oribe, T. Chem. Pharm. Bull 1974, 22, 2767. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5679. Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606. Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.
30. (g) Rh catalysts: Yoshii, E.; Kobayashi, Y.; Koizumi, T.; Oribe, T. Chem. Pharm. Bull 1974, 22, 2767. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5679. Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606. Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.
31. (g) Rh catalysts: Yoshii, E.; Kobayashi, Y.; Koizumi, T.; Oribe, T. Chem. Pharm. Bull 1974, 22, 2767. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5679. Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606. Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.
32. (g) Rh catalysts: Yoshii, E.; Kobayashi, Y.; Koizumi, T.; Oribe, T. Chem. Pharm. Bull 1974, 22, 2767. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5679. Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606. Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.
33. (g) Rh catalysts: Yoshii, E.; Kobayashi, Y.; Koizumi, T.; Oribe, T. Chem. Pharm. Bull 1974, 22, 2767. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5679. Ojima, I.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 2606. Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70.
34. (a) Leutenegger, U.; Madin, A.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1989, 28, 60.
35. (b) von Matt, P.; Pfaltz, A. Tetrahedron: Asymmetry, 1991, 2, 691.
36. (c) Misun, M.; Pfaltz, A. Helv. Chim. Acta 1996, 79, 961.
37. For a recent example of a chiral aldiminato cobalt catalyst for asymmetric reduction of α,β-unsaturated amides, see: Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129.
38. (a) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627.
39. (b) Mon, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573.
40. 2: Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
41. p-tol-BINAP is an abbreviation for 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl; each enantiomer is commercially available.
42. (a) Carter, M. B.; Schiøtt, B.; Gutiérrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667.
43. (b) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640.
44. (c) Mimoun, H.; de Saint Laumer, J. Y.; Giannini, L.; Scopelliti, R.; Floriani, C. J. Am. Chem. Soc. 1999, 121, 6158.
45. (a) Verdaguer, X.; Lange, U. E. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 1998, 37, 1103.
46. (b) Hansen, M. C.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2033.
47. For a discussion of nonlinear effects, see: Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922.
48. Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749.
49. Lorenz, C.; Schubert, U. Chem. Ber. 1995, 128, 1267.
50. Copper enolates have been observed as intermediates in BINAP-copper-catalyzed asymmetric aldol reactions: Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124.
51. (a) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
52. (b) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006.
53. Yoshizumi, T.; Takaya, H. Tetrahedron: Asymmetry 1995, 6, 1253.
54. In preliminary results, we found that, under the same conditions where α,β-unsaturated esters were reduced to saturated esters, α,β-unsaturated ketones were typically overreduced to give saturated alcohols, and an α,β-unsaturated amide was not reduced.