Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to Enones toward the Synthesis of Chiral Phosphines

被引：200

作者：

Feng, Jian-Jun ^{[2
]}

Chen, Xue-Feng ^{[1
]}

Shi, Min ^{[1
,2
]}

Duan, Wei-Liang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 16期

关键词：

P-STEREOGENIC PHOSPHINES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ALDEHYDES; CONJUGATE PHOSPHINATION; CHIROGENIC PHOSPHINE; SECONDARY PHOSPHINES; DIPHENYL PHOSPHITE; ACTIVATED OLEFINS; HYDROPHOSPHINATION;

D O I：

10.1021/ja100606v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric addition of diarylphosphines to B-substituted enones under mild conditions using a chiral pincer-palladium catalyst has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (up to 99% ee).

引用

页码：5562 / +

页数：3

共 38 条

[1]

Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO

[2]

2-6

[3]

[Anonymous], 1999, COMPREHENSIVE ASYMME

[4] Organocatalytic asymmetric hydrophosphination of nitroalkenes [J].

Bartoli, Giuseppe ;

Bosco, Marcella ;

Carlone, Armando ;

Locatelli, Manuela ;

Mazzanti, Andrea ;

Sambri, Letizia ;

Melchiorre, Paolo .

CHEMICAL COMMUNICATIONS, 2007, (07) :722-724

[5] Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity [J].

Blank, Natalia F. ;

Moncarz, Jillian R. ;

Brunker, Tim J. ;

Scriban, Corina ;

Anderson, Brian J. ;

Amir, Omar ;

Glueck, David S. ;

Zakharov, Lev N. ;

Golen, James A. ;

Incarvito, Christopher D. ;

Rheingold, Arnold L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6847-6858

[6]

Borner A., 2008, PHOSPHORUS LIGANDS A, V1-3

[7] Palladium-catalyzed enantioselective allylic phosphination [J].

Butti, Pietro ;

Rochat, Raphael ;

Sadow, Aaron D. ;

Togni, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4878-4881

[8] Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes [J].

Carlone, Armando ;

Bartoli, Giuseppe ;

Bosco, Marcella ;

Sambri, Letizia ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4504-4506

[9] Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines [J].

Chan, Vincent S. ;

Bergman, Robert G. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15122-+

[10] Development of Ruthenium Catalysts for the Enantioselective Synthesis of P-Stereogenic Phosphines via Nucleophilic Phosphido Intermediates [J].

Chan, Vincent S. ;

Chiu, Melanie ;

Bergman, Robert G. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (16) :6021-6032

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