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

被引：31

作者：

Gao, Ying-Xiang ^{[2
,3
]}

Chang, Le ^{[2
,3
]}

Shi, Hang ^{[2
,3
]}

Liang, Bo ^{[2
,3
]}

Wongkhan, Kittiya ^{[1
]}

Chaiyaveij, Duangduan ^{[1
]}

Batsanov, Andrei S. ^{[1
]}

Marder, Todd B. ^{[1
]}

Li, Chuang-Chuang ^{[2
,3
]}

Yang, Zhen ^{[2
,3
]}

Huang, Yong ^{[2
,3
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Peking Univ, Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[3] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, BNLMS,Coll Chem, Beijing 100871, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 11-12期

基金：

美国国家科学基金会; 英国工程与自然科学研究理事会;

关键词：

asymmetric catalysis; catalyst design; enantioselectivity; palladium; thiourea-oxazoline library; ASYMMETRIC BIS(ALKOXYCARBONYLATION) REACTION; HYDRIDE TRANSFER REDUCTION; PAUSON-KHAND REACTION; BIS-ALKOXYCARBONYLATION; CARBONYLATION REACTION; CARBON-MONOXIDE; SILVER-NITRATE; HECK REACTIONS; SUZUKI; COMPLEXES;

D O I：

10.1002/adsc.201000070

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

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.

引用

页码：1955 / 1966

页数：12

共 80 条

[1] Phosphite and thiourea ligand synergy for rhodium catalyzed enantioselective hydroformylation of styrene [J].