Enantioselective enzymatic aminolysis and ammonolysis of dimethyl 3-hydroxyglutarate. Synthesis of (R)-4-amino-3-hydroxybutanoic acid

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 6024-6027

  Puertas, Susana ^a   Rebolledo, Francisca ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 3 HYDROXYBUTYRIC ACID; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS;

EID: 0029839595     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960468d     Document Type: Article

References (22)

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5. For typical examples see: (a) Toone, E. J.; Werth, M. J.; Jones, J. B. J. Am. Chem. Soc. 1990, 112, 4946. (b) Shapira, M.; Gutman, A. L. Tetrahedron: Asymmetry 1994, 5, 1689. (c) Guanti, G.; Banfi, L.; Narisano, E. J. Org. Chem. 1992, 57, 1540. (d) Tsuji, K.; Terao, Y.; Achiwa, K. Tetrahedron Lett. 1989, 30, 6189. (e) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546.
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19. A small amount of rac-3a-c could be obtained when diester 1 and amines (2a-c) were allowed to react in hexane during 9 days in the absence of the enzyme. To obtain rae-3d, diester 1 was dissolved in a solution of ammonia in methanol and the mixture was kept at 5° C during 28 h.
20. 3 as an external standard). For 4b (obtained from optically active 3b) only one signal to -72.04 ppm was observed.
21. Configuration was assigned according to the sign of the previously reported optical rotation for (R)-(+)-monoacid 7: Santaniello, E.; Chiari, M.; Ferraboschi, P.; Trave, S. J. Org. Chem. 1988, 53, 1567.
22. 1H NMR analysis of the obtained mixture of diastereomeric amides.