Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans |
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| Authors: | Robert Chênevert Daniel Goupil Yannick Stéphane Rose Emmanuelle Bédard |
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| Institution: | a Département de chimie, Faculté des sciences et de génie, Université Laval Québec (Qc), G1K 7P4 Canada |
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| Abstract: | The stereoselective acylation of meso-tetrahydropyrans 6 and 7 by enol esters (vinyl acetate or isopropenyl acetate) in the presence of Candida antarctica lipase in organic media gave the corresponding (2R,4S,6S)-monoesters 10 and 11 in high enantiomeric purity. The hydrolysis of the corresponding diacetate derivatives 8 and 9 in the presence of the same enzyme provided the opposite enantiomers, (2S,4R,6R)-monoesters 10 and 11. |
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