Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,2-dimethylcyclohexanone |
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Authors: | Chênevert Robert Lévesque Carine Morin Pierre |
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Affiliation: | Département de Chimie, CREFSIP, Faculté des Sciences et de Genie, Université Laval, Québec (QC), Canada G1K 7P4. robert.chenevert@chm.ulaval.ca |
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Abstract: | The stereoselective acetylation of meso-2,2-dimethyl-1,3-cyclohexanediol by vinyl acetate in the presence of three lipases gave the (1R,3S)-monoester in high enantiomeric excess (ee > or = 98%). The hydrolysis of the corresponding meso-diacetate in the presence of Candida antarctica lipase in phosphate buffer provided the opposite enantiomer. Optically active monoacetates were converted to both enantiomers of 3-hydroxy-2,2-dimethylcyclohexanone, a versatile chiral building block. |
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