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Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule.

ABSTRACT: An unprecedented enantioselective and general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted ?,?-unsaturated butenolides were transformed into the corresponding chiral ?,?-unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the rate-determining step.

SUBMITTER: Wu Y

PROVIDER: S-EPMC3156085 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule.

Wu Yongwei Y Singh Ravi P RP Deng Li L

Journal of the American Chemical Society 20110722 32

An unprecedented enantioselective and general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted β,γ-unsaturated butenolides were transformed into the corresponding chiral α,β-unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the rate-determining step. ...[more]

PMID: 21766859

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