Atropisomers and near-atropisomers: achieving stereoselectivity by exploiting the conformational preferences of aromatic amides

被引:102
作者
Clayden, J [1 ]
机构
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
关键词
D O I
10.1039/b307976g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The conformational preferences of aromatic amides are remarkably easy to control with a high degree of selectivity. This article reviews the consequences of this unusual form of stereocontrol, which enables for example the asymmetric synthesis of atropisomers and the ability to achieve remote stereocontrol by conformational relay.
引用
收藏
页码:127 / 135
页数:9
相关论文
共 87 条
[1]   Barriers to rotation about the chiral axis of tertiary aromatic amides [J].
Ahmed, A ;
Bragg, RA ;
Clayden, J ;
Lai, LW ;
McCarthy, C ;
Pink, JH ;
Westlund, N ;
Yasin, SA .
TETRAHEDRON, 1998, 54 (43) :13277-13294
[2]  
ANDERSEN KK, 1962, TETRAHEDRON LETT, P93
[3]  
[Anonymous], [No title captured]
[4]  
Anstiss M, 2002, SYNLETT, P290
[5]   Synthesis of enantioenriched axially chiral anilides from atropisomerically enriched tartarate ortho-anilides [J].
Ates, A ;
Curran, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5130-5131
[6]   A chiral N-methylbenzamide:: Spontaneous generation of optical activity [J].
Azumaya, I ;
Okamoto, I ;
Nakayama, S ;
Tanatani, A ;
Yamaguchi, K ;
Shudo, K ;
Kagechika, H .
TETRAHEDRON, 1999, 55 (37) :11237-11246
[7]   Dynamic thermodynamic resolution: Control of enantioselectivity through diastereomeric equilibration [J].
Beak, P ;
Anderson, DR ;
Curtis, MD ;
Laumer, JM ;
Pippel, DJ ;
Weisenburger, GA .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (10) :715-727
[8]   DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].
BEAK, P ;
SNIECKUS, V .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312
[9]   DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].
BEAK, P ;
REITZ, DB .
CHEMICAL REVIEWS, 1978, 78 (03) :275-316
[10]   Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].
Beak, P ;
Basu, A ;
Gallagher, DJ ;
Park, YS ;
Thayumanavan, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560