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Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution

✍ Scribed by Csaba Paizs; Petri Tähtinen; Katri Lundell; László Poppe; Florin-Dan Irimie; Liisa T. Kanerva

Book ID
104359837
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
255 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipasecatalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E 100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.

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