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Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst
Author(s) -
Laurell Anna,
Moberg Christina
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100467
Subject(s) - chemistry , kinetic resolution , cyanohydrin , enantiopure drug , enantiomer , enantioselective synthesis , biocatalysis , yield (engineering) , enantiomeric excess , aldehyde , organic chemistry , catalysis , racemization , stereochemistry , reaction mechanism , materials science , metallurgy
A one‐pot recycling procedure comprising Lewis acid catalyzed enantioselective addition of acetyl cyanide to ( E )‐2‐butenal to give the O ‐acetylated cyanohydrin and enzyme‐catalyzed conversion of the minor product enantiomer back to ( E )‐2‐butenal provided essentially enantiopure (2 R ,3 E )‐2‐acetoxy‐3‐pentenenitrile in close to quantitative yield. The opposite enantiomer was obtained, albeit in lower yield and with lower enantiomeric purity than that observed from the minor enantiomer recycling, by dynamic kinetic resolution consisting of reversible addition of HCN to the aldehyde coupled to enzyme‐catalyzed acetylation of the cyanohydrin.