title: 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 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.
authors.affiliation: Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States.
authors.forename: Yongwei
authors.initials: Y
authors.lastname: Wu
authors.forename: Ravi P
authors.initials: RP
authors.lastname: Singh
authors.forename: Li
authors.initials: L
authors.lastname: Deng
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007536:Isomerism; D011522:Protons
chemical_list: D000475:Alkenes; D011522:Protons; C004511:butenolide; D015107:4-Butyrolactone