Enantioselective Michael Reaction of Cyclic β-Ketoesters with Morita-Baylis-Hillman Derivatives Using a Phase-Transfer Catalyst.

J Org Chem

Department of Chemistry, Graduate School of Science , Hiroshima University, 1-3-1 Kagamiyama , Higashi-Hiroshima 739-8526 , Japan.

Published: September 2018

This study aims to develop a highly enantioselective Michael reaction of cyclic β-ketoesters with Morita-Baylis-Hillman (MBH) derivatives using a phase-transfer catalyst. Cyclic β-ketoesters reacted with MBH derivatives to stereoselectively generate a quaternary carbon center in the presence of cinchona alkaloid-derived bulky ammonium catalyst, and aqueous KOH and Michael adducts bearing an acrylate moiety were obtained in good chemical yields with good enantioselectivity.

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http://dx.doi.org/10.1021/acs.joc.8b01777DOI Listing

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