Chemoenzymatic synthesis of both enantiomers of cis-6-(hydroxymethyl)- and cis, cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3178-3180

  Chênevert, Robert ^a   Morin, Marie Pascale ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY 6 (HYDROXYMETHYL)PIPECOLIC ACID; 6 (HYDROXYMETHYL)PIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; ENANTIOMER; ENZYME MECHANISM; HYDROGENATION; HYDROLYSIS; PEPTIDE SYNTHESIS; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0342458264     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823036     Document Type: Article

References (23)

1. (a) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
2. (b) Giannis, A.; Rubsam, F., Adv. Drug Res. 1997, 29, 1.
3. Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 305.
4. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
5. (e) Symposia-in-Print No. 5, Horwell, D. C. (Guest Editor). Bioorg. Med. Chem. Lett. 1993, 3, 797.
6. (a) Filigheddu, S. N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3857.
7. (b) Kahn, M. Synlett 1993, 821.
8. Symposia-in-Print No. 50, Kahn, M. (Guest Editor). Tetrahedron 1993, 49, 3433.
9. Cornish, V. W.; Mendel, D.; Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 621.
10. (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
11. (b) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
12. Duthaler, R. O. Tetrahedron 1994, 50, 1539.
13. Ohfune, Y. Acc. Chem. Res. 1992, 25, 360.
14. (e) Williams, R. M. Organic Chemistry Series: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon: Oxford, 1989.
15. (f) Barrett, G. C. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall, London, 1985.
16. Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332.
17. For a preliminary report, see: Chênevert, R.; Morin, M. P. Tetrahedron: Asymmetry 1996, 7, 2161.
18. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
19. (a) Pavia, M. R. Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M., Kerwin, J. F., Eds.; Wiley: New York, 1998; Chapter 11, pp 213-225.
20. (b) Sofia, M. J.; Hunter, R.; Chan, T. Y.; Vaughan, A.; Dulina, R.; Wang, H.; Gange, D. J. Org. Chem. 1998, 63, 2802.
21. (a) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633.
22. (b) Wang, C. L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 583.
23. Barluenga, J.; Aznar, F.; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918.