Palladium-Catalyzed Efficient Enantioselective Synthesis of Chiral Allenes: Steric and Electronic Effects of Ligands

被引：22

作者：

Wu, Zi ^{[1
]}

Berhal, Farouk ^{[1
]}

Zhao, Mengmeng ^{[2
,3
]}

Zhang, Zhaoguo ^{[2
,3
]}

Ayad, Tahar ^{[1
]}

Ratovelomanana-Vidal, Virginie ^{[1
]}

机构：

[1] Chim ParisTech, Lab Charles Friedel, UMR CNRS 7223, F-75231 Paris 05, France

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[3] State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ACS CATALYSIS | 2014年 / 4卷 / 01期

关键词：

allene; synthetic method; asymmetric catalysis; enantioselective; palladium; ASYMMETRIC TRANSFER HYDROGENATION; KINETIC RESOLUTION; DIFLUORPHOS; DERIVATIVES; SYNPHOS; COMPLEXES; ROUTE; HYDROSILYLATION; PROSTAGLANDIN; DIPHOSPHINES;

D O I：

10.1021/cs4007827

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Asymmetric synthesis of chiral allenes starting from prochiral substrates under mild reaction conditions promoted by Pd-SYNPHOS catalyst is reported. This protocol provides an efficient access to various enantioenriched aryl- and alkyl- substituted allenes, which are versatile building blocks of high utility to both organic and medicinal chemists, in excellent isolated yields (up to 96%) and high enatiomeric ratio values (up to 95:5). In addition, a comparative study using several C-2-symmetric atropisomeric diphosphine ligands revealed the overwhelming impact of the steric and electronic properties of the ligands for the catalytic efficiency of this process.

引用

页码：44 / 48

页数：5

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