Lewis Acid Mediated (3+2) Cycloadditions of Donor-Acceptor Cyclopropanes with Heterocumulenes

被引：141

作者：

Goldberg, Alexander F. G. ^{[1
]}

O'Connor, Nicholas R. ^{[1
]}

Craig, Robert A., II ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

RING-OPENING REACTIONS; ENANTIOSELECTIVE SYNTHESIS; MECHANISM; ALDEHYDES; NITRONES;

D O I：

10.1021/ol302494n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isocyanates, isothiocyanates, and carbodiimides are effective substrates in (3 + 2) cycloadditions with donor-acceptor cyclopropanes for the synthesis of five-membered heterocycles. These reactions exhibit a broad substrate scope, high yields, and well-defined chemoselectivity. Discussed herein are the implications of Lewis acid choice on the stereochemical outcome and the reaction mechanism.

引用

页码：5314 / 5317

页数：4

共 30 条

[1] THE FIRST ENANTIOSPECIFIC PALLADIUM-CATALYZED CYCLOADDITION OF AZIRIDINES AND HETEROCUMULENES - NOVEL SYNTHESIS OF CHIRAL 5-MEMBERED RING HETEROCYCLES [J].