A convenient and efficient ring-opening reaction of aziridines with acetylenes and synthesis of dihydropyrroles

被引：55

作者：

Ding, CH

Dai, LX

Hou, XL

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2005年 / 61卷 / 40期

基金：

中国国家自然科学基金;

关键词：

alkynylation; aziridine; ring-opening; cyclization; dihydropyrrole;

D O I：

10.1016/j.tet.2005.07.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of 'BuOK, reaction of acetylenes with N-Ts substituted aziridines derived from both cyclic and acyclic alkenes at room temperature gave rise to homopropargylamines in good to high yields and in high regioselectivity. Not only Ph- and Me3Si-substituted acetylenes but also acetylene itself was suitable reagents. Treatment of ring-opening products with I-2 and AgOAc in the presence of K2CO3 provided dihydropyrroles in high yields. One-pot synthesis of dihydropyrroles was also realized by the reaction of aziridines and phenylacetylene in the presence of NaH followed by the treatment with I-2 and AgOAc. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：9586 / 9593

页数：8

共 44 条

[1] Stereoselective synthesis of erythro beta-substituted aspartates [J].