Catalysis of benzoin condensation by conformationally-restricted chiral bicyclic thiazolium salts

被引：68

作者：

Dvorak, CA

Rawal, VH

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

[2] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(98)00439-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new conformationally-restricted chiral bicyclic thiazolium salts have been synthesized by a concise, high-yielding route. These salts are effective catalysts for the benzoin condensation, affording benzoin in 20-30% yield, with a similar range of enantiomeric excesses. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2925 / 2928

页数：4

相关论文

共 18 条

[1] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[2] STUDIES ON MODEL SYSTEMS FOR THIAMINE ACTION - SYNTHESIS OF REACTIVE INTERMEDIATES, AND EVIDENCE ON THE FUNCTION OF THE PYRIMIDINE RING [J].

BRESLOW, R ;

MCNELIS, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (12) :3080-3082

[3] The mechanism of thiazolium catalysis [J].

Breslow, R ;

Schmuck, C .

TETRAHEDRON LETTERS, 1996, 37 (45) :8241-8242

[4] THE SYNTHESIS OF 4-CHLOROMETHYLTHIAZOLE HYDROCHLORIDE AND BETA-(4-THIAZOLYL)-ALANINE HYDROCHLORIDE [J].

CALDWELL, WT ;

FOX, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) :2935-2936

[5]

DVORAK CA, 1998, THESIS U CHICAGO

[6] THE REACTION OF STYRENE OXIDE WITH SULFONAMIDES [J].

JOHNSON, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (08) :2336-2337

[7] Synthesis of and asymmetric induction by chiral bicyclic thiazolium salts [J].

Knight, RL ;

Leeper, FJ .

TETRAHEDRON LETTERS, 1997, 38 (20) :3611-3614

[8] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[9] A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].

KOLB, HC ;

SHARPLESS, KB .

TETRAHEDRON, 1992, 48 (48) :10515-10530

[10] INTRODUCTION TO A RATIONAL DESIGN OF CHIRAL THIAZOLIUM SALTS [J].

MARTI, J ;

CASTELLS, J ;

LOPEZCALAHORRA, F .

TETRAHEDRON LETTERS, 1993, 34 (03) :521-524