A Room-Temperature Catalytic Asymmetric Synthesis of Allenes with ECNU-Phos

被引：130

作者：

Wang, Yuli ^{[1
]}

Zhang, Wanli ^{[1
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 31期

基金：

中国国家自然科学基金;

关键词：

OPTICALLY-ACTIVE ALLENES; ENANTIOSELECTIVE SYNTHESIS; RACEMIZATION; 2,3-ALLENOATES; REDUCTION;

D O I：

10.1021/ja406135t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three-carbon axial chirality has been asymmetrically established from racemic one-carbon central chirality efficiently at room temperature: we report here the discovery of the first catalytic asymmetric carbonylation of readily available racemic propargylic carbonates to access optically active 2,3-allenoates with fairly high ee. The combination of [(pi-allyl)PdCl](2) with [(R)-ECNU-Phos], a new chiral bisphosphine ligand based on a biphenyl skeleton, demonstrates high enantioselectivity. Both enantiomers of allenoates can be obtained at room temperature by applying either (R)- or (S)-ECNU-Phos.

引用

页码：11517 / 11520

页数：4

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