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

作者:Wu Yongwei; Singh Ravi P; Deng Li*
来源:Journal of the American Chemical Society, 2011, 133(32): 12458-12461.
DOI:10.1021/ja205674x

摘要

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.

  • 出版日期2011-8-17