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

被引：58
|
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
收藏
页码：11900 / 11907
页数：8
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