Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates.: Part 1:: Formation of cis-aziridines

被引：26

作者：

Sweeney, JB

Cantrill, AA

McLaren, AB

Thobhani, S

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Univ Reading, Sch Chem, Reading RG6 6AD, Berks, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

aza-Darzens; aziridination; imine; camphorsultam;

D O I：

10.1016/j.tet.2006.01.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Theaza-Darzens ('ADZ') reactions off-diphenylphosphinyl (W-Dpp') imines with chiral enolates derived from oxazolidinones and camphorsultam have been Studied. Whilst oxazolidinone enolates reacted poorly in terms of aziridination, the use of the chiral enolate derived from both antipodes of N-bromoacetyl 2, 10-camphorsultam, 2R-(5) and 2S-(5), with N-diphehenylphosphinyl aryl and tert-butylimines proceeded in generally good yield to give, respectively, (2'R,3'R)- or (2'S,3'S)-cis-N-diphenylphosphinyl aziridinoyl sultams of high de. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3681 / 3693

页数：13

共 40 条

[1] METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL ALPHA-HALOGENATED IMIDE ENOLATES - A STEREOCONTROLLED CHIRAL EPOXIDE SYNTHESIS [J].