A stereodivergent approach to chiral nonracemic N-protected α,α-dialkylated amino acids

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12106-12107

  Spino, Claude ^a   Gobdout, Cédrickx ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PEPTIDE SYNTHESIS; PHASE TRANSITION; PROTEIN CONFORMATION; STEREOCHEMISTRY;

ALDEHYDES; ALKYLATION; AMINO ACIDS; PENTANOIC ACIDS; STEREOISOMERISM; VALINE;

EID: 0141992718     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037078a     Document Type: Article

References (31)

1. (a) Hsieh, K. H.; Marsall, G. R. J. Med. Chem. 1986, 29, 1968-1971.
2. (b) Samanen, J.; Narindray, D.; Adams, W., Jr.; Cash, T.; Yellin, T.; Regoli, D. J. Med. Chem. 1988, 31, 510-516.
3. (c) Formaggio, F.; Pantano, M.; Crisma, M.; Toniolo, C.; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J.; Becker, E. I. Bioorg. Med. Chem. Lett. 1993, 3, 953-956.
4. (d) Bellier, B.; McCort-Tranchepain, I.; Ducos, B.; Danascimento, S.; Meudal, H.; Noble, F.; Garbay, C.; Roques, B. P. J. Med. Chem. 1997, 40, 3947-3956.
5. (a) Karle, I.; Kaul, R.; Roa, R. B.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 12048-12054.
6. (b) Karle, I.; Roa, R. B.; Prasad, S.; Kaul, R.; Balaram, P. J. Am. Chem. Soc. 1994, 116, 10355-10361.
7. (c) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Précigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072.
8. (d) Hodgkin, E. E.; Clark, J. D.; Miller, K. R.; Marshall, G. R. Biopolymers 1990, 30, 533-546.
9. (a) Shirlin, D.; Gerhart, F.; Hornsperger, J. M.; Harmon, M.; Wagner, I. ; Jung, M. J. Med. Chem. 1988, 31, 30-36.
10. (b) Zhelyaskov, D. K.; Levitt, M.; Uddenfriend, S. Mol. Pharmacol. 1968, 4, 445-451.
11. (c) Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382.
12. (a) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635.
13. (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599 and references therein.
14. (c) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
15. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
16. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids: Pergamon Press: Oxford, 1989.
17. Spino, C.; Beaulieu, C. Angew. Chem., Int. Ed. 2000, 39, 1930-1932.
18. (a) Negishi, E.-i.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639-6647.
19. (b) Negishi, E.-i.; Kondakov, D. Y.; Choueiry, D.; Kasai, K.; Takahashi, T. J. Am. Chem. Soc. 1996, 118, 9577-9588.
20. (c) Negishi, E.; Tamotsu, T. Aldrichimica Acta 1985, 18, 31-48.
21. 3. See: Spino, C.; Granger, M.-C.; Tremblay, M.-C. Org. Lett. 2002, 4, 4735-4737.
22. (a) Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1-11.
23. (b) Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 227-232.
24. (c) Wong, T.; Tjepkema, M. W.; Audrain, H.; Wilson, P D.; Fallis, A. G. Tetrahedron Lett. 1996, 37, 755-758.
25. (d) Forgione, P.; Fallis, A. G. Tetrahedron Lett. 2000, 41, 11-15.
26. For examples of the use of similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417.
27. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947.
28. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152.
29. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872.
30. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732.
31. (f) Tanaka, M.; Oba, M.; Tamai, K; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.