Asymmetric catalytic routes to chiral building blocks of medicinal interest

Pure and Applied Chemistry

Volumn 68, Issue 1, 1996, Pages 37-44

  Burk, Mark J ^a   Gross, Michael F ^a   Harper, T Gregory P ^a   Kalberg, Christopher S ^a   Lee, Jeffrey R ^a   Martinez, Jose P ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002022909     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668010037     Document Type: Article

References (40)

1. (a) Ojima, I. (Ed.) Catalytic Asymmetric Synthesis, VCH Publishers: Weinheim, 1993. Chapter 2.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley & Sons: New York, 1994, Chapter 2.
3. (a) Burk. M.J.; Feaster, J.E.; Harlow, R.L. Organometallics 1990, 9, 2653.
4. (b) Burk, M.J.; Harlow, R.L. Angew. Chemie Int. Ed. Engl. 1990, 29, 1462.
5. (c) Burk, M.J.; Feaster, J.E.; Harlow, R.L. Tetrahedron: Asymmetry 1991, 2, 569.
6. (a) Burk, M.J. J. Am. Chem. Soc. 1991, 113, 8518.
7. (b) Burk, M.J.; Feaster, J.E. J. Am. Chem. Soc. 1992, 114, 6266.
8. (c) Burk, M.J.; Feaster, J.E.; Nugent, W.A.; Harlow, R.L. J. Am. Chem. Soc. 1993, 115, 10125.
9. (d) Burk, M.J.; Martinez, J.P.; Feaster, J.E.; Cosford, N. Tetrahedron (Symposium-In-Print) 1994, 50, 4399.
10. (e) Burk, M.J.; Feng, S.G.; Gross, M.F.; Tumas, W. J. Am. Chem. Soc. 1995, 117, In Press
11. Burk, M.J.; Harper, T.G.P; Kalberg, C.S. J. Am. Chem. Soc. 1995, 117, 4423.
12. (a) Williams, R.M. Synthesis of Optically Active α-Amino Acids Pergamon: New York, 1989.
13. (b) Coppola, G.M.; Schuster, H.F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley and Sons, New York, 1987.
14. Roberts, D.C.; Vellaccio, F. "Unusual α-Amino Acids in Peptide Synthesis," In The Peptides; Gross, E.; Meienhofer, J. (eds.); Academic Press: New York, 1983, Chapter 6.
15. Fauchère, J.-L. (Ed.) QSAR: Quantitative Structure-Activity Relationships in Drug Design, Alan R. Liss, Inc.: New York, 1989.
16. Hansch, C.; Leo, A.; Unger, S.H.; Kim, K.H.; Nikaitani, D.; Lien, E.J. J. Med. Chem. 1973, 16, 1207.
17. Porter, J.; Dykert, J.; Rivier, J. Int. J. Peptide Protein Res. 1987, 30, 13.
18. Burk, M.J.; Martinez, J.P.; Lee, J.R. J. Am. Chem. Soc. 1994, 776, 10847.
19. Hawthorne, M.F. Angew. Chem. Int. Ed. Engl. 1993, 32, 950.
20. (a) Snyder, H.R.; Reedy, A.J.; Lennarz, W.J. J. Am. Chem. Soc. 1958, 80, 835.
21. (b) Roberts, D.C.; Suda, K.; Samanen, J.; Kemp, D.S. Tetrahedron Lett. 1980, 21, 3435.
22. (c) Coderre, J.A.; Glass, J.D.; Fairchild, R.G.; Roy, U.; Cohen. S.; Fand, I. Cancer Res. 1987, 47, 6377.
23. (d) Takahashi, H.; Yoshino, K.; Maruyama, T.; Mori, Y. Chem. Abs. 1994, 121, 83900j.
24. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487.
25. Burk, M.J.; Martinez, J.P.; Straub, J.A., Manuscript in preparation.
26. (a) Koenig, K.E. "Applicability of Asymmetric Hydrogenation," In Asymmetric Synthesis: Morrison, J.D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 3.
27. (b) 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.
28. (c) Achiwa, K. Tetrahedron Lett. 1978, 2583.
29. Burk, M.J.; Gross, M.F.; Martinez, J.P. J. Am. Chem. Soc. 1995, In Press.
30. (a) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
31. (b) Jones, B.A.; Yamaguchi, M.; Patten, A.; Danishefsky, S.J.; Ragan, J.A.; Smith, D.B.: Schreiber, S.L. J. Org. Chem, 1989, 54, 19.
32. (c) Ohashi, T.; Hasegawa, J. In Chirality in Industry Collins, A.N.; Sheldrake, G.N.; Crosby, J. (eds.), Wiley: New York, Chapters 12 and 13.
33. (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
34. (b) Taber. D.F.; Silverberg, L.J. Tetrahedron Lett. 1991, 32, 4227.
35. (c) King, S.A.; Thompson. A.S.; King, A.O.; Verhoeven, T.R. J. Org. Chem. 1992, 57, 6689.
36. Burk, M.J.; Harper, T.G.P.; Lee, J.R.; Kalberg. C. Tetrahedron Lett. 1994, 35, 4963. See also: Tani, K.; Suwa, K.; Tanigawa, E.; Yoshida, T.; Okano, T.; Otsuka, S. Chem. Lett. 1982, 261.
37. Burk, M.J.; Harper, T.G.P.; Lee, J.R.; Kalberg. C. Tetrahedron Lett. 1994, 35, 4963. See also: Tani, K.; Suwa, K.; Tanigawa, E.; Yoshida, T.; Okano, T.; Otsuka, S. Chem. Lett. 1982, 261.
38. (a) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
39. (b) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144.
40. (c) Genêt, J.-P.; Can̄o de Andrade, M.C.; Ratovelomanana-Vidal, V. Tetrahedron Lett. 1995, 36, 2063.