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A Thiourea‐Oxazoline Library with Axial Chirality: Ligand Synthesis and Studies of the Palladium‐Catalyzed Enantioselective Bis(methoxycarbonylation) of Terminal Olefins
Author(s) -
Gao YingXiang,
Chang Le,
Shi Hang,
Liang Bo,
Wongkhan Kittiya,
Chaiyaveij Duangduan,
Batsanov Andrei S.,
Marder Todd B.,
Li ChuangChuang,
Yang Zhen,
Huang Yong
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000070
Subject(s) - oxazoline , chemistry , enantioselective synthesis , palladium , thiourea , catalysis , ligand (biochemistry) , axial chirality , carbonylation , chirality (physics) , yield (engineering) , combinatorial chemistry , organic chemistry , medicinal chemistry , receptor , biochemistry , chiral symmetry breaking , physics , materials science , quantum mechanics , carbon monoxide , quark , nambu–jona lasinio model , metallurgy
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% ee under optimized conditions.