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Ionic Acylating Agents for the Enzymatic Resolution of sec ‐Alcohols in Ionic Liquids
Author(s) -
Lourenço Nuno M. T.,
Monteiro Carlos M.,
Afonso Carlos A. M.
Publication year - 2010
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.201000640
Subject(s) - chemistry , ionic liquid , kinetic resolution , alkyl , yield (engineering) , biocatalysis , enantiomer , acylation , carboxylate , organic chemistry , ionic bonding , resolution (logic) , enantioselective synthesis , catalysis , ion , metallurgy , artificial intelligence , computer science , materials science
Potential acylating agents containing pendant ionic groups have been screened for the enzymatic kinetic resolution of rac ‐secondary alcohols in ionic liquids with CAL‐B as biocatalyst. This study has allowed the identification of the 1‐methyl‐3‐alkylimidazolium cation attached to a carboxylate group through a C 10 ‐alkyl chain as an efficient acylating agent for this transformation. This strategy was applied to the resolution of 2‐hydroxycyclohexanecarbonitrile in which the 1 R ,2 S enantiomer was isolated in 35 % ee (73 % yield) and the 1 S ,2 R enantiomer in 97 % ee (23 % yield).