Asymmetric Synthesis of P-Stereogenic Diarylphosphinites by Palladium-Catalyzed Enantioselective Addition of Diarylphosphines to Benzoquinones

被引：119

作者：

Huang, Yinhua ^{[1
,2
]}

Li, Yongxin ^{[1
]}

Leung, Pak-Hing ^{[1
]}

Hayashi, Tamio ^{[2
,3
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[3] ASTAR, Inst Mat Res & Engn, Singapore 117602, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 13期

关键词：

CHIRAL PHOSPHORUS LIGANDS; STEREOSPECIFIC SYNTHESIS; SECONDARY PHOSPHINES; ACTIVATED OLEFINS; HYDROPHOSPHINATION; RESOLUTION; ALKYLATION; COMPLEXES; BORANE; 1,6-ADDITION;

D O I：

10.1021/ja501007t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of phenyl(2,4,6-trimethylphenyl)phosphine with a substituted benzoquinone in the presence of a chiral phosphapalladacycle complex as a catalyst and triethylamine in chloroform at -45 degrees C proceeded in a new type of addition manner to give a high yield of a 4-hydroxyphenyl phenyl(2,4,6-trimethylphenyl)phosphinite with 98% enantioselectivity, which is a versatile intermediate readily convertible into various phosphines and their derivatives with high enantiomeric purity.

引用

页码：4865 / 4868

页数：4

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