Lewis acid-catalyzed Friedel-Crafts/Michael cascade reaction of N,N-dialkyl-3-vinylanilines with N-tosylaziridines for the stereoselective synthesis of highly functionalized tetrahydroisoquinolines

被引：9

作者：

Lee, Sang Gyu ^{[1
]}

Sin, Seunghui ^{[1
]}

Kim, Seungyeon ^{[1
]}

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Dept Chem, 154-42 Gwanggyosan Ro, Suwon 16227, South Korea

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

Friedel-Crafts reaction; Michael addition; Cascade reaction; Tetrahydroisoquinoline; N-Tosylaziridine; ASYMMETRIC 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; AZIRIDINES; 1,2,3,4-TETRAHYDROISOQUINOLINES; CYCLIZATION; ALDEHYDES;

D O I：

10.1016/j.tetlet.2018.03.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis acid-catalyzed Friedel-Crafts/Michael cascade reaction between N-dialkyl-3-vinylanilines and N-tosylaziridines has been developed for the stereoselective synthesis of tetrahydroisoquinolines (THIQs). The reaction using Gd(OTf)(3) as the Lewis acid catalyst was tolerant to the various N-dialkyl-3-vinylaniline and N-tosylaziridine substrates and provided access to 28 new, highly functionalized THIQs in typically high yields with moderate- to- excellent diastereoselectivities. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1480 / 1483

页数：4

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