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
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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