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A Copper(I)-Catalyzed Addition/Annulation Sequence for the Two-Component Synthesis of γ-Ylidenebutenolides

Sangwon Seo and Michael C. Willis*

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K., Email: michael.willischem.ox.ac.uk

S. Seo, M. C. Willis, Org. Lett., 2017, 19, 4556-4559.

DOI: 10.1021/acs.orglett.7b02151 (free Supporting Information)


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Abstract

A highly efficient Cu(I)-catalyzed addition/annulation sequence enables the synthesis of (Z)-ylidenebutenolides from readily available α-ketoacids and alkynes. The reaction displays good substrate scope, and delivers products with high stereoselectivity. The ylidenebutenolides can be converted into a diverse range of heterocycles.

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Derivatization of γ-Ylidenebutenolides to Other Heterocycles



Key Words

butenolides


ID: J54-Y2017