Ionic acylating agents for the enzymatic resolution of sec-alcohols in ionic liquids
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 C10-alkyl chain as an efficient acylating agent for this transformation. This strategy was applied to the resolution of 2-hydroxycyclohexanecarbonitrile in which the 1R,2S enantiomer was isolated in 35 % ee (73 % yield) and the 1S,2R enantiomer in 97 % ee (23 % yield). 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 theidentification of the 1-methyl-3-alkylimidazolium cation attached to a carboxylate group through a C10-alkyl chain as an efficient acylating agent for this transformation. Copyright
Lourenco, Nuno M. T.,Monteiro, Carlos M.,Afonso, Carlos A. M.
experimental part
p. 6938 - 6943
(2011/02/24)
Separation of secondary alcohols via enzymatic kinetic resolution using fatty esters as reusable acylating agents
A two consecutive step procedure for the resolution-separation of secondary alcohols employing ethyl tetradecanoate in the presence of lipase allowed the enzymatic kinetic resolution of two target molecules, 1-phenylethanol and 6-methylhept-5-en-2-ol. (S)-1-Phenylethanol was isolated in a yield of 47% with an ee of 94% and (R)-1-phenylethanol in a yield of 51% with an ee of 95%. (S)-6-Methylhept-5-en-2-ol was isolated in a yield 47% and an ee of 87% and (R)-6-methylhept-5-en-2-ol in a yield 49% and an ee of 90%.
Monteiro, Carlos M.,Lourenco, Nuno M.T.,Afonso, Carlos A.M.
experimental part
p. 952 - 956
(2010/08/06)
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