Issue 3, 2003

Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis–Hillman adducts

Abstract

Catalysed by the nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 cells, a number of β-aryl- and β-alkyl- β-hydroxy-α-methylenepropiononitriles (the Baylis–Hillman nitriles) 1 underwent hydrolysis under mild conditions to produce the corresponding enantiomerically enriched Baylis–Hillman amides 2 and acids 3. The enantioselectivity of the biotransformations was strongly determined by the steric effect of the substituents at the β-position of the substrates. The protection of the free hydroxy of β-phenyl-β-hydroxy-α-methylenepropiononitrile 1a by methylation led to the enhancement of enantiocontrol of the biohydrolysis.

Graphical abstract: Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis–Hillman adducts

Article information

Article type
Paper
Submitted
08 Oct 2002
Accepted
14 Nov 2002
First published
23 Dec 2002

Org. Biomol. Chem., 2003,1, 535-540

Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis–Hillman adducts

M. Wang and Y. Wu, Org. Biomol. Chem., 2003, 1, 535 DOI: 10.1039/B209791E

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