Hydrolase-catalysed preparation of chiral alpha,alpha-disubstituted cyanohydrin acetates

The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of alpha,alpha-disubstituted cyanohydrin acetates, a type of protected tertiary alcohols th...

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Bibliographic Details
Published in:Advanced Synthesis & Catalysis
Main Authors: Holt, Jarle, Arends, Isabel W. C. E., Minnaard, Adriaan J., Hanefeld, Ulf
Format: Article in Journal/Newspaper
Language:English
Published: 2007
Subjects:
asymmetric catalysis
cyanohydrins
enzyme catalysis
hydrolases
kinetic resolution
tertiary alcohols
ENZYMATIC KINETIC RESOLUTION
CHEMOENZYMATIC SYNTHESIS
PROTECTED CYANOHYDRINS
CANDIDA-ANTARCTICA
LIPASE-A
ACID
ENANTIOSELECTIVITY
ESTERS
Rugosa
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11370/403d6bae-0dd2-4645-b8f1-c8c8713d8d58
https://research.rug.nl/en/publications/403d6bae-0dd2-4645-b8f1-c8c8713d8d58
https://doi.org/10.1002/adsc.200700053
Description
Summary:The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of alpha,alpha-disubstituted cyanohydrin acetates, a type of protected tertiary alcohols that form particularly interesting building blocks in organic synthesis. Utilising Subtilisin A the hydrolysis reaction was (S)-selective, while Candida rugosa lipase was (R)-selective. With these commercially available enzymes both enantiomers of the cc,a-disubstituted cyanohydrin acetates are now accessible.

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