Highly Enantioselective Hydrogenation of (E)-β-(Acylamino)acrylates Catalyzed by Rh(I)-Complexes of Electron-Rich P-Chirogenic Diphosphines

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1701-1704

  Yasutake, Masaya ^a   Gridnev, Ilya D ^a   Higashi, Natsuka ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; ELECTRON; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ACRYLATES; CATALYSIS; ELECTRONS; HYDROGENATION; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHINES; STEREOISOMERISM;

EID: 0035979049     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0158967     Document Type: Article

References (33)

1. (a) Noyori, R. Asymmetric Catalysys in Organic Synthesis; John Wiley & Sons: New York, 1994.
2. (b) Brown, J. M. Hydrogenation of Functionalized Carbon-Carbon Double Bonds; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp 119-182.
3. (c) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley: New York, 2000.
4. (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
5. (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
6. (b) Cole, D. C. Tetrahedron. 1994, 50, 9517.
7. (c) Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447.
8. (a) Deng, Li.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320.
9. (b) Wang, Z.-M.; Kolb, H. C.; Sharpless, K. B. J. Org. Chem. 1994, 59, 5104.
10. (c) Guenard, D.; Voegelein, F. G.; Potier, P. Acc. Chem. Res. 1993, 26, 160.
11. (a) Hattori, K.; Miyata, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151.
12. (a) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455.
13. (b) Juaristi, E.; Escalante, J.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1992, 57, 2396.
14. (c) Seebach, D.; Overhand, M.; Kühnle, Martinonni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
15. (d) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
16. (a) Achiwa, K.; Soga, T. Tetrahedron Lett. 1978, 13, 1119.
17. (b) Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y. Chem. Pharm. Bull. 1979, 27, 2223.
18. Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
19. Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907.
20. (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
21. (b) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988.
22. (c) Gridnev, I. D.; Yamanoi, Y.; Higashi, N.; Tsuruta, H.; Yasutake, M.; Imamoto, T. Adv. Synth. Catal. 2001, 343, 118.
23. (a) Gridnev, I. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183.
24. (b) Gridnev, I. D.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 10486.
25. (c) Gridnev, I. D.; Imamoto, T. Organometallics 2001, 20, 545-549.
26. (d) Gridnev, I. D.; Yasutake, M.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc., in press.
27. 2 to result in low to moderate S-enantioselection.
28. (a) Chan, A. S. C.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 838.
29. (b) Brown, J. M.; Chaloner, P. A J. Chem. Soc., Chem. Commun. 1980, 344.
30. P-P = 12 Hz).
31. (a) Landis, C. R.; Feldgus, S. Angew. Chem., Int. Ed. 2000, 39, 2863.
32. (b) Feldgus, S.; Landis, C. R. J. Am. Chem. Soc. 2000, 122, 12714.
33. Feldgus, S.; Landis, C. R. Organometallics 2001, in press; we gratefully acknowledge Professor Clark Landis' kind sharing of information prior to publication.