Regio- and Stereoselective Copper-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Terminal Allenes.

Org Lett

Ecole Nationale Supérieure de Chimie de Montpellier , Institut Charles Gerhardt Montpellier UMR 5253 CNRS, AM2N , 8 rue de l'Ecole Normale , Montpellier 34296 Cedex 5, France.

Published: April 2018

Simple ligand-free copper systems were found as efficient catalysts for the addition of 1,3-dicarbonyl compounds to N-allenyl derivatives. This highly regio- and stereoselective reaction has been accomplished in the presence of malonates, 1,3-ketoesters, and 1,3-diketones with good to excellent yields under mild conditions. This methodology represents the first allylation of 1,3-dicarbonyl compounds with allenes catalyzed by copper.

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http://dx.doi.org/10.1021/acs.orglett.8b00575DOI Listing

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