Preparation of enantiopure 4-arylmandelic acids via a Pd/C catalysed Suzuki coupling of enantiopure 4-bromomandelic acid

被引：46

作者：

Dyer, UC ^{[1
]}

Shapland, PD ^{[1
]}

Tiffin, PD ^{[1
]}

机构：

[1] Roche Discovery Welwyn, Chem Synthesis Dept, Welwyn Garden City AL7 3AY, Herts, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 09期

关键词：

Suzuki reaction; biaryl compounds; 4-bromomandelic acid; palladium on carbon;

D O I：

10.1016/S0040-4039(00)02304-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A library of enantiomerically pure mandelic acid derivatives has been prepared using a palladium on carbon catalysed Suzuki reaction. The chirality was derived from enantiomerically pure 4-bromomandelic acid which was obtained by resolution with alpha -methylbenzylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1765 / 1767

页数：3

共 12 条

[1] Antispasmodics. V
Blicke, FF
Grier, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 : 1725 - 1728
[2] Application of automation and thermal analysis to resolving agent selection
Dyer, UC
Henderson, DA
Mitchell, MB
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (03) : 161 - 165
[3] Multikilogram-scale synthesis at a biphenyl carboxylic acid derivative using a Pd/C-mediated Suzuki coupling approach
Ennis, DS
McManus, J
Wood-Kaczmar, W
Richardson, J
Smith, GE
Carstairs, A
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) : 248 - 252
[4] One-step synthesis of biphenylacetic acids via Pd/C-catalyzed arylation
Gala, D
Stamford, A
Jenkins, J
Kugelman, M
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (02) : 163 - 164
[5] ARYL COUPLINGS WITH HETEROGENEOUS PALLADIUM CATALYSTS
MARCK, G
VILLIGER, A
BUCHECKER, R
[J]. TETRAHEDRON LETTERS, 1994, 35 (20) : 3277 - 3280
[6] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483
[7] A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides
Old, DW
Wolfe, JP
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9722 - 9723
[8] QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS INVOLVING THE INHIBITION OF GLYCOLIC ACID OXIDASE BY DERIVATIVES OF GLYCOLIC AND GLYOXYLIC ACIDS
RANDALL, WC
STREETER, KB
CRESSON, EL
SCHWAM, H
MICHELSON, SR
ANDERSON, PS
CRAGOE, EJ
WILLIAMS, HWR
EICHLER, E
ROONEY, CS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (06) : 608 - 614
[9] OPTIMIZED STILLE COUPLING REACTIONS CATALYZED BY PALLADIUM ON CARBON WITH CUI AS COCATALYST
ROTH, GP
FARINA, V
LIEBESKIND, LS
PENACABRERA, E
[J]. TETRAHEDRON LETTERS, 1995, 36 (13) : 2191 - 2194
[10] Catalytic cross-coupling reactions in biaryl synthesis
Stanforth, SP
[J]. TETRAHEDRON, 1998, 54 (3-4) : 263 - 303

← 1 2 →