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Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives

Yuyu Cheng, Yuzhe Han and Pengfei Li*

*Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Boulevard, Nanshan District, Shenzhen, Guangdong 518055, China, Email: lipfsustc.edu.cn

Y. Cheng, Y. Han, P. Li, Org. Lett., 2017, 19, 4774-4777.

DOI: 10.1021/acs.orglett.7b02144 (free Supporting Information)


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Abstract

A chiral phosphine-catalyzed enantioselective [1 + 4] annulation of Morita-Baylis-Hillman carbonates with β,γ-unsaturated α-keto esters and α,β-unsaturated ketones provides a wide range of optically active 2,3-dihydrofurans in high yields with excellent asymmetric induction via a Michael alkylation process.

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proposed mechanism



Key Words

2,3-Dihydrofurans, Organocatalysis


ID: J54-Y2017