4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 18, Pages 11191-11203

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01777

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan (JSPS KAKENHI) [JP26410121]

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This study aims to develop a highly enantioselective Michael reaction of cyclic beta-ketoesters with Morita-Baylis-Hillman (MBH) derivatives using a phase-transfer catalyst. Cyclic beta-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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