Enantioselective Preparation of ω-Functionalized O-Acylated Cyanohydrins

A minor enantiomer recycling one-pot process usingω-functionalized prochiral aldehydes as starting materials and two reinforcing catalysts has been reported. The desired aldehyde for these process studies was 5-bromo-1-pentanal. In a two-phase solvent system, enzyme-catalyzed hydrolysis of the minor...

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Bibliographic Details
Main Author: Heid, Berenice
Format: Others
Language:English
Published: KTH, Skolan för kemivetenskap (CHE) 2011
Subjects:
Online Access:http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-40896
Description
Summary:A minor enantiomer recycling one-pot process usingω-functionalized prochiral aldehydes as starting materials and two reinforcing catalysts has been reported. The desired aldehyde for these process studies was 5-bromo-1-pentanal. In a two-phase solvent system, enzyme-catalyzed hydrolysis of the minor enantiomer regenerates continuously the prochiral starting material and Lewis acid catalysed addition of acetyl cyanide provides the O-acetylated cyanohydrins. The minor enantiomer recycling process has been studied and improved for 5-bromo-1-pentanal to receive high enantiomeric excess and yield of the expected O-acetylated cyanohydrin.