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. 2018 Sep 21;83(18):11191-11203.
doi: 10.1021/acs.joc.8b01777. Epub 2018 Aug 31.

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

Ryukichi Takagi  1 , Emi Fujii  1 , Hirotoshi Kondo  1
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Enantioselective Michael Reaction of Cyclic β-Ketoesters with Morita-Baylis-Hillman Derivatives Using a Phase-Transfer Catalyst

Ryukichi Takagi et al. J Org Chem. .

Abstract

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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