Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H[hair space])-one. New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route

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Jelle Brinksma, Hanneke van der Deen, Arjan van Oeveren and Ben L. Feringa


Abstract

A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R[hair space])-5-Acetoxyfuran-2(5H[hair space])-one (12) was obtained with ee > 99% in a multigram scale catalytic esterification using immobilized lipase PS. The addition of lithiated dithianes to chiral synthon 12 was followed by an effective multistep reduction to produce enantiomerically pure benzylbutyrolactones.


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