Highly practical and enantioselective Cu-catalyzed conjugate addition of alkylzinc reagents to cyclic enones at ambient temperature

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3201-3203

  Krauss, Isaac J ^a   Leighton, James L ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CRYSTAL; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE;

EID: 0141744738     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034983r     Document Type: Article

References (24)

1. Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427-2430.
2. (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
3. (b) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521.
4. (c) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263.
5. (d) Shintani, R.; Fu, G. C. Org. Lett. 2002, 4, 3699-3702.
6. (e) Liang, L.; Au-Yeung, T. T.-L.; Chan, A. S. C. Org. Lett. 2002, 4, 3799-3801.
7. (f) Zhou, H.; Wang, W.-H.; Fu, Y.; Xie, J.-H.; Shi, W.-J.; Wang, L.-X.; Zhou, Q.-L. J. Org. Chem. 2003, 68, 1582-1584.
8. For recent reviews, see: (g) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (h) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (i) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258.
9. For recent reviews, see: (g) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (h) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (i) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258.
10. For recent reviews, see: (g) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (h) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (i) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258.
11. (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756.
12. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781.
13. (c) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
14. (d) Degrado, S. J., Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
15. This class of ligand is known and has been investigated in several asymmetric catalytic reactions. See: (a) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999-1002. (b) Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291-292. (c) Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927-934. (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777. (e) Gustafsson, M.; Bergqvist, K.-E.; Frejd, T. J. Chem. Soc., Perkin Trans. 1 2001, 1452-1457.
16. This class of ligand is known and has been investigated in several asymmetric catalytic reactions. See: (a) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999-1002. (b) Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291-292. (c) Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927-934. (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777. (e) Gustafsson, M.; Bergqvist, K.-E.; Frejd, T. J. Chem. Soc., Perkin Trans. 1 2001, 1452-1457.
17. This class of ligand is known and has been investigated in several asymmetric catalytic reactions. See: (a) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999-1002. (b) Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291-292. (c) Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927-934. (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777. (e) Gustafsson, M.; Bergqvist, K.-E.; Frejd, T. J. Chem. Soc., Perkin Trans. 1 2001, 1452-1457.
18. This class of ligand is known and has been investigated in several asymmetric catalytic reactions. See: (a) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999-1002. (b) Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291-292. (c) Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927-934. (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777. (e) Gustafsson, M.; Bergqvist, K.-E.; Frejd, T. J. Chem. Soc., Perkin Trans. 1 2001, 1452-1457.
19. This class of ligand is known and has been investigated in several asymmetric catalytic reactions. See: (a) Okada, T.; Morimoto, T.; Achiwa, K. Chem. Lett. 1990, 999-1002. (b) Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291-292. (c) Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927-934. (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777. (e) Gustafsson, M.; Bergqvist, K.-E.; Frejd, T. J. Chem. Soc., Perkin Trans. 1 2001, 1452-1457.
20. Hoveyda has documented a similar effect in the reactions of acyclic enones. See ref 3b.
21. A kinetic resolution of chiral 2-cyclohexenones based on this type of reaction has been reported. See: Naasz, R.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 927-930.
22. Satoh, T.; Kaneko, Y.; Okuda, T.; Uwaya, S.; Yamakawa, K. Chem. Pharm. Bull. 1984, 32, 3452-3460.
23. Feringa has reported examples of catalyst control with chiral enones. No measure of the "intrinsic" diastereofacial bias of these enones was reported. See: Imbos, R.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2001, 57, 2485-2489.
24. For a comprehensive review on nonlinear effects, see: Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2952.