A Thiourea-Oxazoline Library with Axial Chirality: Ligand Synthesis and Studies of the Palladium-Catalyzed Enantioselective Bis(methoxycarbonylation) of Terminal Olefins

作者:Gao, Ying-Xiang; Chang, Le; Shi, Hang; Liang, Bo; Wongkhan, Kittiya; Chaiyaveij, Duangduan; Batsanov, Andrei S.; Marder, Todd B.*; Li, Chuang-Chuang; Yang, Zhen; Huang, Yong
来源:Advanced Synthesis & Catalysis, 2010, 352(11-12): 1955-1966.
DOI:10.1002/adsc.201000070

摘要

We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2-phenylsuccinates were obtained in >90% yield and up to 84% cc under optimized conditions.