Chemoenzymatic synthesis of both enantiomers of cis-6-hydroxymethylpipecolic acid

Tetrahedron Asymmetry

Volumn 7, Issue 8, 1996, Pages 2161-2164

  Chênevert, Robert ^a   Morin, Marie Pascale ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXYMETHYLPIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS NIGER; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030220431     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00260-1     Document Type: Article

References (26)

1. 1. a) Vinic, F.J. Approaches to the Discovery of Non-Peptide Ligands for Peptide Receptors and Peptidases. In Annual Reports in Medicinal Chemistry. Allen, R.C, Ed. Academic Press, San Diego, 1989. Vol. 24, chap. 26, pp. 243-252.
2. b) Synthesis of Peptidomimetics. In Medicinal Chemistry for the 21st Century, Wermuth, C.G. Ed. Blackwell Scientific Publications, London, 1992, chap. 15-18, pp. 215-277.
3. c) Liskamp, R.M.J. Angew. Chem. Int. Ed. Engl., 1994, 33, 305.
4. d) Gante, J. Angew. Chem. Int. Ed. Engl., 1994, 33, 1699.
5. 2. Cornish, V.W.; Mendel, D.; Schultz, P.G. Angew. Chem. Int. Ed. Engl., 1995, 34, 621.
6. 3. a) Jackson, R.F.W.; Palmer, N.J.; Wythes, M.J.; Clegg, W.; Elsegood, M.R.J. J. Org. Chem., 1995, 60, 6431.
7. b) Hegedus, L.S. Acc. Chem. Res., 1995, 28, 299.
8. c) Kazmaier, U.; Krebs, A. Angew. Chem., Int. Ed. Engl., 1995, 34, 2012.
9. d) Cole, D.C. Tetrahedron, 1994, 50, 9517.
10. e) Kessler, H.; Von Roedern, E.G. Angew. Chem. Int. Ed. Engl., 1994, 33, 687.
11. f) Karle, I.L.; Rao, R.B.; Prasad, S.; Kaul, R.; Balaram, P. J. Am. Chem. Soc., 1994, 116, 10355.
12. g) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc., 1994, 116, 799.
13. h) Duthaler, R.O. Tetrahedron, 1994, 50, 1539.
14. i) Ohfune, Y. Acc. Chem. Res., 1992, 25, 360.
15. j) Williams, R.M. Synthesis of Optically Active α-Amino Acids; Organic Chemistry Series; Baldwin, J.E.; Magnus, P.D. Eds.; Pergamon Press, Oxford, 1989, Vol. 7.
16. 4. a) Chênevert, R.; Dickman, M. Tetrahedron: Asymmetry, 1992, 3, 1021.
17. b) Chênevert, R.; Dickman, M.; Morin, M.P. Preparative Biotransformations; Roberts, S.M.; Wiggins, K.; Casy, G. (eds.); Wiley, 1995, section 1.5, pp. 16-21.
18. 5. a) Schoffers, E.; Golebiowski, A.; Johnson, C.R. Tetrahedron, 1996, 52, 3769.
19. b) Theil, F. Chem. Rev. 1995, 95, 2203.
20. c) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
21. d) Faber, K.; Riva, S. Synthesis, 1992, 895.
22. e) Chen, C.S.; Sih, C. Angew. Chem. Int. Ed. Engl., 1989, 28, 695.
23. 6. Carlsen, P.H.J; Katsuki, T.; Martin, V.S.; Sharpless, K.B. J. Org. Chem., 1981, 46, 3936.
24. 2O).
25. 8. Absence of epimerisation/racemisation has been confirmed by NMR analysis of Mosher's esters of N-benzylmethyl esters of (+) and (-)-4.
26. 9. Bolos, J.; Gubert, S.; Anglada, L.; Pérez, A.; Sacristan, A.; Ortiz, J.A. J. Heterocyclic Chem. 1994, 31, 1493.