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Highly Enantioselective and Anti-Diastereoselective Catalytic Intermolecular Glyoxylate-Ene Reactions: Effect of the Geometrical Isomers of Alkenes

Xiang Zhang, Min Wang, Ran Ding, Yun-He Xu* and Teck-Peng Loh*

*Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: xyh0709ustc.edu.cn, teckpengntu.edu.sg

X. Zhang, M. Wang, R. Ding, Y.-H. Xu, T.-P. Loh, Org. Lett., 2015, 17, 2736-2739.

DOI: 10.1021/acs.orglett.5b01151 (free Supporting Information)


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Abstract

An In(III)-catalyzed intermolecular glyoxylate-ene reaction enables an efficient synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities. Only alkene isomers having a proton β-cis to the substituent reacted in this catalytic system.

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Key Words

homoallylic alcohols, Alder-Ene Reaction


ID: J54-Y2015