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Stereospecific microbial reduction of ethyl 1-benzyl-3-oxo-piperidine-4-carboxylate

Authors :
Richard M. Corbett
Animesh Goswami
Zhiwei Guo
Ramesh N. Patel
Bharat P. Patel
Source :
Tetrahedron: Asymmetry. 17:2015-2020
Publication Year :
2006
Publisher :
Elsevier BV, 2006.

Abstract

Microbial reduction of ethyl 1-benzyl-3-oxo-piperidine-4-carboxylate by the majority of evaluated microorganisms gave the ethyl cis-(3R,4R)-1-benzyl-3R-hydroxy-piperidine-4R-carboxylate as the major product in high diastereo- and enantioselectivities. The 3R,4R-hydroxy ester was produced in 97.4% diastereomeric excess (de) and 99.8% enantiomeric excess (ee) by Candida parapsilosis SC16347, while 99.5% de and 98.2% ee were obtained from reduction by Pichia methanolica SC16415. A few of the evaluated microorganisms gave 10–40% of the ethyl trans-(3R,4S)-1-benzyl-3R-hydroxy-piperidine-4S-carboxylate as the minor product.

Details

ISSN :
09574166
Volume :
17
Database :
OpenAIRE
Journal :
Tetrahedron: Asymmetry
Accession number :
edsair.doi...........b1c0889c67997382ced5b6e8e6c8e250