Catalytic imino Diels-Alder reaction by triflic imide and its application to one-pot synthesis from three components

被引：59

作者：

Takasu, Kiyosei ^{[1
]}

Shindoh, Naoya ^{[1
]}

Tokuyama, Hidetoshi ^{[1
]}

Ihara, Masataka ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 51期

关键词：

imino Diels-Alder reaction; substituted piperidines; triflic imide; three component reaction;

D O I：

10.1016/j.tet.2006.09.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An imino Diels-Alder reaction of 2-siloxydienes with aldimines catalyzed by triflic imide (Tf2NH; 0.1 similar to 10 mol % amount) has been developed leading to substituted piperidin-4-ones. Tf2NH catalyst is compatible with basic functions, such as pyridine and indole rings in the imino Diels-Alder reaction. Furthermore, X-ray crystallographic analysis indicates that trans-2,6-diphenyl-4-piperidinone 4a obtained by this reaction has a unique conformation in the solid state. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：11900 / 11907

页数：8

共 34 条

[31] Silver-catalyzed [2+2] cycloadditions of siloxy alkynes [J].