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

共 58 条

[41] Palladium-catalyzed asymmetric phosphination: Enantioselective synthesis of a P-chirogenic phosphine [J].

Moncarz, JR ;

Laritcheva, NF ;

Glueck, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13356-13357

[42] Asymmetric synthesis of P-stereogenic o-hydroxyaryl-phosphine (borane) and phosphine-phosphinite ligands [J].

Moulin, D ;

Bago, S ;

Bauduin, C ;

Darcel, C ;

Jugé, S .

TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :3939-3956

[43] Optical resolution and the study of ligand effects on the ortho-metalation reaction of resolved (±)-diphenyl[1-(1-naphthyl)ethyl]phosphine and its arsenic analogue [J].

Ng, JKP ;

Tan, GK ;

Vittal, JJ ;

Leung, PH .

INORGANIC CHEMISTRY, 2003, 42 (23) :7674-7682

[44]

Ohashi A, 2002, EUR J ORG CHEM, V2002, P2535

[45]

Ojima I., 2010, CATALYTIC ASYMMETRIC

[46]

OMELANCZUK J, 1980, J CHEM SOC CHEM COMM, P24

[47] PREPARATION OF SCALEMIC P-CHIRAL PHOSPHINES AND THEIR DERIVATIVES [J].

PIETRUSIEWICZ, KM ;

ZABLOCKA, M .

CHEMICAL REVIEWS, 1994, 94 (05) :1375-1411

[48] Enantioselective addition of secondary phosphines to methacrylonitrile: Catalysis and mechanism [J].

Sadow, AD ;

Togni, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :17012-17024

[49] Nickel(II)-catalyzed highly enantioselective hydrophosphination of methacrylonitrile [J].

Sadow, AD ;

Haller, I ;

Fadini, L ;

Togni, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14704-14705

[50] Platinum-catalyzed asymmetric alkylation of secondary phosphines: Enantioselective synthesis of P-stereogenic phosphines [J].

Scriban, C ;

Glueck, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2788-2789

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