Rotational features of carbon-nitrogen bonds in axially chiral o-tert-butyl anilides and related molecules.: Potential substrates for the 'prochiral auxiliary' approach to asymmetric synthesis

被引：113

作者：

Curran, DP ^{[1
]}

Hale, GR

Geib, SJ

Balog, A

Cass, QB

Degani, ALG

Hernandes, MZ

Freitas, LCG

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[2] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 23期

基金：

巴西圣保罗研究基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0957-4166(97)00599-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new strategy for asymmetric induction termed the 'prochiral auxiliary' approach is introduced. Reactions of acylating agents with prochiral N-methyl-o-tert-butyl aniline provide anilides that are axially chiral by virtue of restricted rotation about the N-Ar bond, Rotamer populations about the amide bond (E/Z) were studied by H-1 NMR. Several pairs of enantiomeric o-tert-butyl anilides were separated by chiral chromatography and barriers about the N-Ar bond were measured by thermal racemization. Related o-(1-(trialkylsilyloxy)-1-methylethyl) anilides were also studied. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：3955 / 3975

页数：21

共 47 条

[1]

[Anonymous], 1996, Asymmetric Synthesis

[2] STEREOCHEMISTRY OF BENZANILIDES AND N-METHYLBENZANILIDES [J].