Organocatalytic [4+2] addition reactions via tetraenamine intermediate

被引：54
|
作者：
Stiller, Julian [1 ]
Poulsen, Pernille H. [1 ]
Cruz, David Cruz [1 ]
Dourado, Jorge [1 ]
Davis, Rebecca L. [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
来源：
CHEMICAL SCIENCE | 2014年 / 5卷 / 05期
关键词：
DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; ASYMMETRIC ORGANOCATALYSIS; DIENAMINE CATALYSIS; TRIENAMINES; 2,4-DIENALS; ACTIVATION; CONSTRUCTION; PRINCIPLE; OXINDOLES;
D O I：
10.1039/c4sc00081a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The [4+2]-cycloaddition reaction of 3-olefinic oxindoles with a tetraenamine intermediate is presented. In the reaction, a novel class of highly functionalized spirocyclic cyclohexanes with four stereocenters is formed in high yield and excellent stereoselectivity. Mechanistic investigations and calculations point to a stepwise mechanism involving tetraenamine intermediates. Furthermore, several transformations are presented.
引用
收藏
页码：2052 / 2056
页数：5
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