Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 32, Pages 12458-12461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja205674x
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- National Institute of Health [GM-61591]
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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 beta,gamma-unsaturated butenolides were transformed into the corresponding chiral alpha,beta-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.
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