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

Author:
Takagi, Ryukichi, Fujii, Emi, Kondo, Hirotoshi
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 11191-11203
ISSN:
1520-6904
Subject:
Cinchona, ammonium, carbon, catalysts, chemical reactions, enantioselectivity, moieties, organic compounds, potassium hydroxide
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.
Agid:
6146221