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Issue 24, 1998
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Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H )-one. New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route

Abstract

A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R )-5-Acetoxyfuran-2(5H )-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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Article information


J. Chem. Soc., Perkin Trans. 1, 1998, 4159-4164
Article type
Paper

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

J. Brinksma, H. van der Deen, A. van Oeveren and B. L. Feringa, J. Chem. Soc., Perkin Trans. 1, 1998, 4159
DOI: 10.1039/A805777J

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