Non-linear effects operate and dynamic ligand exchange occurs when chiral BINOL-boron Lewis acids are used for asymmetric catalysis

被引：21

作者：

Cros, JP ^{[1
]}

Peréz-Fuertes, Y ^{[1
]}

Thatcher, MJ ^{[1
]}

Arimori, S ^{[1
]}

Bull, SD ^{[1
]}

James, TD ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(03)00352-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Non-linear effects reveal that the use of chiral BINOL-boron reagents for aza-Diels-Alder reactions results in an enantioselective catalytic species containing at least 2 equiv. of BINOL. Dynamic ligand exchange and ligand accelerated catalysis occurs in these reactions, consistent with the formation of a cyclic borate ester of BINOL with enhanced Lewis acidity. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1965 / 1968

页数：4

相关论文

共 27 条

[1] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070

[2]

Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2923, DOI 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO

[3]

2-1

[4] NOVEL ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS WITH 3-(1'-HYDROXYETHYL) SUBSTITUENTS - BORON REAGENT MEDIATED ALDOL REACTION OF CHIRAL IMINES AND SILYL KETENE ACETALS DERIVED FROM 3-HYDROXYBUTYRATE [J].

HATTORI, K ;

YAMAMOTO, H .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2337-2342

[5] HIGHLY SELECTIVE AND OPERATIONALLY SIMPLE SYNTHESIS OF ENANTIOMERICALLY PURE BETA-AMINO ESTERS VIA DOUBLE STEREODIFFERENTIATION [J].

HATTORI, K ;

MIYATA, M ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1151-1152

[6]

HATTORI K, 1993, SYNLETT, P239

[7]

HATTORI K, 1993, SYNLETT, P129

[8] ASYMMETRIC AZA-DIELS-ALDER REACTION MEDIATED BY CHIRAL BORON REAGENT [J].

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3264-3265

[9] ASYMMETRIC AZA-DIELS-ALDER REACTION - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REACTION OF IMINE MEDIATED BY CHIRAL LEWIS ACID [J].

HATTORI, K ;

YAMAMOTO, H .

TETRAHEDRON, 1993, 49 (09) :1749-1760

[10] PRACTICAL PREPARATION OF ALPHA-HYDROXY-BETA-AMINO ESTER UNITS STEREOSELECTIVE SYNTHESIS OF TAXOL SIDE-CHAIN AND NORSTATINE [J].

HATTORI, K ;

YAMAMOTO, H .

TETRAHEDRON, 1994, 50 (09) :2785-2792