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

被引:117
|
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
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
收藏
页码:4865 / 4868
页数:4
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