Asymmetrization of all -cis-3,5-dihydroxy-1-(methoxycarbonyl)cyclohexane and of the 4-methyl and 4-ethyl substituted homologues

Enantiomerically pure mono acylated derivatives of cis, cis-3,5-dihydroxy-1-(methoxycarbonyl)cyclohexane 1, all- cis-3,5-dihydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 2 and all- cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane 3 were obtained upon lipase catalyzed asymmetrization. PPL-ca...

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Published inTetrahedron: asymmetry Vol. 11; no. 19; pp. 3887 - 3900
Main Authors Zhao, Yurui, Wu, Yusheng, De Clercq, Pierre, Vandewalle, Maurits, Maillos, Philippe, Pascal, Jean-Claude
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 06.10.2000
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Summary:Enantiomerically pure mono acylated derivatives of cis, cis-3,5-dihydroxy-1-(methoxycarbonyl)cyclohexane 1, all- cis-3,5-dihydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 2 and all- cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane 3 were obtained upon lipase catalyzed asymmetrization. PPL-catalyzed transesterification of 1 with vinyl acetate led in high yield to the ( S)-monoacetate (+)- 13. With substrates 2 and 3 this process was slower and gave the ( R)-monoacetates (−)- 14 and (−)- 15; the best results were obtained with SAM II lipase. On the other hand, enantiotoposelective hydrolysis of their diacetates and especially dibutyrates gave useful results only for the 4-substituted substrates and produced the ( S)-monoesters.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)00339-6