Resolution of Diols with C2-Symmetry by Lipase Catalysed Transesterification

Article abstract of DOI:10.1016/S0957-4166(00)80133-0

S-Ethyl thiooctanoate was used as acyl donor in the transesterification of 2,3-butanediol (1), 2,4-pentanediol (2), and 2,5-hexanediol (3), catalysed by a lipase from Candida antarctica.Mixtures of all stereoisomers were used as substrates in each case. 2,5-Hexanediol was transesterified with high stereoselectivity and the (2S,5S)-2,5-hexanediol was isolated in good yield with >99percent ee.The diester of (2R,5R)-2,5-hexanediol was formed in good yield and was hydrolysed to yield the (2R,5R)-2,5-hexanediol of high enantiomeric excess (>99percent ee).Similar results were obtainedfor 2,4-pentanediol with >99percent ee for both enantiomers.The stereoselectivity for 2,3-butanediol was lower than for 2 and 3, giving 89percent ee for the R,R-enantiomer and 34percent ee for the S,S-enantiomer.