Dysprosium(III) catalyzed formation of hexahydrofuro[3,2-c]quinolines via 2:1 coupling of dihydrofuran with substituted anilines

被引：58

作者：

Batey, RA ^{[1
]}

Powell, DA ^{[1
]}

Acton, A ^{[1
]}

Lough, AJ ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 45期

基金：

加拿大自然科学与工程研究理事会;

关键词：

quinolines; hetero Diels-Alder; lanthanides; imines; oxonium ions; oxepins; multi-component coupling;

D O I：

10.1016/S0040-4039(01)01726-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel dysprosium(III) catalyzed 2:1 coupling reaction between substituted anilines and 2 equiv. of dihydrofuran that yields substituted hexahydrofuro[3.2-c]quinolines is described. The reaction proceeds via a formal Diets-Alder process between an in situ generated 2-azadiene with another equivalent of dihydrofuran and may proceed either through a stepwise or an asynchronous concerted mechanism. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：7935 / 7939

页数：5

共 22 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2] Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes [J].