Optically active axially chiral anilide and maleimide derivatives as new chiral reagents: Synthesis and application to asymmetric Diels-Alder reaction

被引：130

作者：

Kitagawa, O

Izawa, H

Sato, K

Dobashi, A

Taguchi, T

Shiro, M

机构：

[1] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 19203, Japan

[2] Rigaku Corp, Akishima, Tokyo 196, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 08期

关键词：

D O I：

10.1021/jo9721711

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New axially chiral N-acryl-N-allyl-o-tert-butylanilide and N-(o-tert-butylphenyl)-2-methylmaleimide with high optical purity and definite absolute configurations were prepared from o-tert-butylaniline and (S)-O-acetyl lactic acid or (R)-2-methylsuccinic acid, respectively. Iodine-or Lewis acid-mediated asymmetric Diels-Alder reaction of these axially chiral compounds with various dienes proceeded with high endo and diastereofacial selectivity.

引用

页码：2634 / 2640

页数：7

共 27 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2]

ARAI Y, 1988, CHEM PHARM BULL, V36, P4162

[3] DIASTEREOISOMERIC ATROPISOMERS FROM THE ADDITION OF LITHIATED N,N-DIALKYL-1-NAPHTHAMIDES TO ALDEHYDES [J].