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...
Published in: | Advanced Synthesis & Catalysis |
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Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2007
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Subjects: | |
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 |
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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