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Asymmetric Synthesis of α,β-Unsaturated δ-Lactones through Copper(I)-Catalyzed Direct Vinylogous Aldol Reaction

Hai-Jun Zhang, Liang Yin*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: liangyinsioc.ac.cn

H.-J. Zhang, L. Yin, J. Am. Chem. Soc., 2018, 140, 12270-12279.

DOI: 10.1021/jacs.8b07929 (free Supporting Information)


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Abstract

A Cu(I)-catalyzed direct vinylogous aldol reaction (DVAR) of β,γ-unsaturated esters and various aldehydes enables a synthesis of chiral α,β-unsaturated δ-lactones. For aromatic aldehydes, a one-pot reaction consisting of DVAR, isomerization of the unsaturated carbon-carbon double bond, and subsequent intramolecular transesterification was required, whereas for α,β-unsaturated and aliphatic aldehydes, the reaction proceeded directly.

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Key Words

5,6-Dihydropyran-2-ones


ID: J48-Y2018