Asymmetric pinacol coupling of aromatic aldehydes with TiCl2/enantiopure amine or hydrazine reagents

被引：45

作者：

Enders, D ^{[1
]}

Ullrich, EC ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(00)00379-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric pinacol coupling of aromatic aldehydes under homogeneous conditions with TiCl2 in the presence of enantiopure amines or hydrazines afforded 1,2-diols in moderate to excellent yields with good dl-diastereoselectivities and enantioselectivities in the range of 6-65% ee. A non-linear temperature effect ('principle of isoinversion') has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3861 / 3865

页数：5

共 42 条

[1] Stereoselective pinacol coupling in aqueous media [J].

Barden, MC ;

Schwartz, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5484-5485

[2]

BRIENNE MJ, 1978, J CHEM RES-S, P60

[3] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY [J].

BUSCHMANN, H ;

SCHARF, HD ;

HOFFMANN, N ;

ESSER, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) :477-515

[4]

BUSCHMANN H, 1991, ANGEW CHEM, V103, P480

[5] PINACOLIC COUPLING OF AROMATIC-ALDEHYDES AND KETONES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE IN BASIC-MEDIA [J].

CLERICI, A ;

PORTA, O .

TETRAHEDRON LETTERS, 1982, 23 (34) :3517-3520

[6] A highly dl-stereoselective pinacolization of aromatic aldehydes mediated by titanium trichloride in dichloromethane [J].

Clerici, A ;

Clerici, L ;

Porta, O .

TETRAHEDRON LETTERS, 1996, 37 (17) :3035-3038

[7] An efficient protocol for Sharpless-style racemic dihydroxylation [J].

Eames, J ;

Mitchell, HJ ;

Nelson, A ;

O'Brien, P ;

Warren, S ;

Wyatt, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :1095-1103

[8]

ENDERS D, 1995, SYNTHESIS-STUTTGART, P659

[9] ASYMMETRIC SYNTHESIS VIA METALATED CHIRAL HYDRAZONES - ENANTIOSELECTIVE ALKYLATION OF CYCLIC-KETONES AND ALDEHYDES [J].

ENDERS, D ;

EICHENAUER, H .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08) :2933-2960

[10] Catalytic asymmetric hydrosilylation with (triazolinylidene)rhodium complexes containing an axis of chirality [J].

Enders, D ;

Gielen, H ;

Breuer, K .

TETRAHEDRON-ASYMMETRY, 1997, 8 (21) :3571-3574

← 1 2 3 4 5 →