Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio

被引：104

作者：

Castanet, AS ^{[1
]}

Colobert, F ^{[1
]}

Broutin, PE ^{[1
]}

Obringer, M ^{[1
]}

机构：

[1] Univ Strasbourg 1, Lab Stereochim, ECPM, CNRS,UMR 7008, F-67087 Strasbourg 2, France

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(02)00169-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Suzuki cross-coupling reaction with sterically hindered arylboronic acids is reported. Good yields are obtained by using DME and cesium fluoride in the presence of Pd(OAc)(2) and triphenylphosphine. The catalytic asymmetric reaction between 2-methoxy-1-naphthylboronic acid and 1-iodo-2-methoxynaphthalene was studied in the presence of a palladium-chiral phosphine catalyst. When the reaction was carried out with Pd(OAc), and (R)-BINAP (versus (R)-TolBINAP), the enantioselection was dramatically influenced by the phosphine palladium ratio. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：659 / 665

页数：7

共 53 条

[1] SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].

ALCOCK, NW ;

BROWN, JM ;

HULMES, DI .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756

[2] RATES AND MECHANISMS OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES GENERATED IN-SITU FROM MIXTURES OF PD0(DBA)2 AND TRIPHENYLPHOSPHINE [J].

AMATORE, C ;

JUTAND, A ;

KHALIL, F ;

MBARKI, MA ;

MOTTIER, L .

ORGANOMETALLICS, 1993, 12 (08) :3168-3178

[3] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].

AMATORE, C ;

JUTAND, A ;

MBARKI, MA .

ORGANOMETALLICS, 1992, 11 (09) :3009-3013

[4] A modified in situ Suzuki cross-coupling of haloarenes for the preparation of C-2-symmetric biaryls [J].

Andersen, NG ;

Maddaford, SP ;

Keay, BA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9556-9559

[5] Investigations into ambient temperature biaryl coupling reactions [J].

Anderson, JC ;

Namli, H ;

Roberts, CA .

TETRAHEDRON, 1997, 53 (44) :15123-15134

[6]

ANDERSON JC, 1995, SYNLETT, P765

[7] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].

Bringmann, G ;

Breuning, M ;

Tasler, S .

SYNTHESIS-STUTTGART, 1999, (04) :525-558

[8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[9] ON THE MECHANISM OF THE FORMATION OF "S(-)-(1,1'-BINAPHTHALENE)-2,2'-DIOL VIA COPPER(II)AMINE COMPLEXES [J].

BRUSSEE, J ;

GROENENDIJK, JLG ;

TEKOPPELE, JM ;

JANSEN, ACA .

TETRAHEDRON, 1985, 41 (16) :3313-3319

[10] The first asymmetric Suzuki cross-coupling reaction [J].

Cammidge, AN ;

Crépy, KVL .

CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724

← 1 2 3 4 5 6 →