Asymmetric Catalytic Synthesis of β-Branched Amino Acids via Highly Enantioselective Hydrogenation Reactions

Journal of the American Chemical Society

Volumn 117, Issue 36, 1995, Pages 9375-9376

  Burk, Mark J ^a   Gross, Michael F ^a   Martinez, Jose P ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029080089     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00141a039     Document Type: Article

References (27)

1. Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH Publishers: Weinheim, 1993; Chapter 2.
2. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994; Chapter 2.
3. Knowles, W.S. Acc. Chem. Res. 1983, 16, 106.
4. Koenig, K.E. Applicability of Asymmetric Hydrogenation. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 3.
5. Scott, J.W.; Kieth, D.D.; Nix, G.; Parrish, D.R.; Remington, S.; Roth, G.P.; Townsend, J.M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086.
6. Riley, D.P.; Shumate, R.E. J. Org. Chem. 1980, 45, 5187.
7. Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.
8. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326.
9. Achiwa, K. Tetrahedron Lett. 1978, 2583.
10. Roberts, D.C.; Vellaccio, F. Unusual a-Amino Acids in Peptide Synthesis. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1983; Chapter 6.
11. Hruby, V.J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
12. Burk, M.J.; Feaster, J.E.; Harlow, R.L. Tetrahedron: Asymmetry 1991, 2, 569.
13. Burk, M.J. J. Am. Chem. Soc. 1991, 113, 8518.
14. Burk, M.J.; Feaster, J.E. J. Am. Chem. Soc. 1992, 114, 6266.
15. Burk, M.J.; Martinez, J.P.; Feaster, J.E.; Cosford, N. Tetrahedron (Symposium-In-Print) 1994, 50, 4399.
16. Burk, M.J.; Harper, T.G.P.; Kalberg, C.S. J. Am. Chem. Soc. 1995, 117, 4423.
17. Burk, M.J.; Feaster, J.E.; Nugent, W.A.; Harlow, R.L. J. Am. Chem. Soc. 1993, 115, 10125.
18. Williams, R.M. Synthesis of Optically Active α- Amino Acids; Pergamon: New York, 1989.
19. Lung, F.-D.; Li, G.; Lou, B.-S.; Hruby, V. J. Synth. Commun. 1995, 25, 57.
20. Josien, H.; Lavielle, S.; Brunissen, A.; Saffroy, M.; Torrens, Y.; Beaujouan, J.-C.; Glowinski, J.; Chassaing, G. J. Med. Chem. 1994, 37, 1586.
21. Nicolas, E.; Russell, K.C.; Knollenberg, J.; Hruby, V.J. J. Org. Chem. 1993, 58, 7565.
22. Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733.
23. Huang, Z.; He, Y.-B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. J. Am. Chem. Soc. 1992, 114, 9390.
24. Toth, G.; Russell, K.C.; Landis, G.; Kramer, T.H.; Fang, L.; Knapp, R.; Davis P.; Burks, T.F.; Yamamura, H.I.; Hruby, V.J. J. Med. Chem. 1992, 35, 2384.
25. Hruby, V.J.; Toth, G.; Gehrig, C.A.: Kao, L.F.; Knapp, R.; Lui, G.K.; Yamamura, H.I.; Kramer, T.H.; Davis, P.; Burks, T.F. J. Med. Chem. 1991, 34, 1823.
26. Samanen, J.; Narindray, D.; Cash, T.; Brandeis, E.; Adams, W., Jr.; Yellin, T.; Eggleston, D.; DeBrosse, C.; Regoli, D. J. Med. Chem. 1989, 32, 466.
27. Okubo, K.; Izumi, Y. Bull. Chem. Soc. Jpn. 1970, 43, 1541.