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

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

共 50 条

[1] Palladium-Catalyzed Enantioselective CH Arylation for the Synthesis of P-Stereogenic Compounds
Lin, Zi-Qi
Wang, Wei-Zhen
Yan, Shao-Bai
Duan, Wei-Liang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (21) : 6265 - 6269
[2] Enantioselective synthesis of P-stereogenic benzophospholanes via palladium-catalyzed intramolecular cyclization
Brunker, Tim J.
Anderson, Brian J.
Blank, Natalia F.
Glueck, David S.
Rheingold, Arnold L.
ORGANIC LETTERS, 2007, 9 (06) : 1109 - 1112
[3] Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to Enones toward the Synthesis of Chiral Phosphines
Feng, Jian-Jun
Chen, Xue-Feng
Shi, Min
Duan, Wei-Liang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) : 5562 - +
[4] Palladium-catalyzed asymmetric addition of diarylphosphines to N-tosylimines
Huang, Miao
Li, Chun
Huang, Jian
Duan, Wei-Liang
Xu, Sheng
CHEMICAL COMMUNICATIONS, 2012, 48 (90) : 11148 - 11150
[5] P-Stereogenic PCP Pincer-Pd Complexes: Synthesis and Application in Asymmetric Addition of Diarylphosphines to Nitroalkenes
Ding, Boqiang
Zhang, Zhenfeng
Xu, Yang
Liu, Yangang
Sugiya, Masashi
Imamoto, Tsuneo
Zhang, Wanbin
ORGANIC LETTERS, 2013, 15 (21) : 5476 - 5479
[6] Chirality breeding via asymmetric phosphination. Palladium-catalyzed diastereoselective synthesis of a P-stereogenic phosphine
Blank, NF
McBroom, KC
Glueck, DS
Kassel, WS
Rheingold, AL
ORGANOMETALLICS, 2006, 25 (07) : 1742 - 1748
[7] Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand
Taylor, Alexander M.
Altman, Ryan A.
Buchwald, Stephen L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (29) : 9900 - +
[8] P-stereogenic P/N hybrid ligands: a remarkable switch in enantioselectivity in palladium-catalyzed asymmetric allylation
Danjo, H
Higuchi, M
Yada, M
Imamoto, T
TETRAHEDRON LETTERS, 2004, 45 (03) : 603 - 606
[9] ORGN 582-Development of an enantioselective palladium-catalyzed cross-coupling of silylphosphines for the synthesis of P-stereogenic phosphines
Chan, Vincent S.
Bergman, Robert G.
Toste, F. Dean
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[10] Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis
Wei, Xu
Lu, Junzhu
Duan, Wei-Liang
SYNTHESIS-STUTTGART, 2016, 48 (23): : 4155 - 4160

← 1 2 3 4 5 →