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Asymmetric Olefin Isomerization of Butenolides via Proton Transfer Catalysis by an Organic Molecule

Yongwei Wu, Ravi P. Singh and Li Deng*

*Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States, Email: dengbrandeis.edu

Y. Wu, R. P. Singh, L. Deng, J. Am. Chem. Soc., 2011, 133, 12458-12461.

DOI: 10.1021/ja205674x (free Supporting Information)



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Abstract

A biomimetic proton transfer catalysis with a chiral organic catalyst enabled an enantioselective olefin isomerization of a broad range of mono- and disubstituted β,γ-unsaturated butenolides into the corresponding chiral α,β-unsaturated butenolides in high enantioselectivity and yield. Mechanistic studies have revealed the protonation as the rate-determining step.

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Key Words

Butenolides, Organocatalysis


ID: J48-Y2011-2250