Organocatalytic Asymmetric Domino Aza-Michael-Mannich Reaction: Synthesis of Tetrahydroimidazopyrimidine Derivatives

被引：33
|
作者：
Li, Hong [1 ]
Zhao, Junling [1 ]
Zeng, Lili [1 ]
Hu, Wenhui [1 ,2 ]
机构：
[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510530, Guangdong, Peoples R China
[2] State Key Lab Resp Dis, Guangzhou 510120, Guangdong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 19期
关键词：
DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; ORGANIC CATALYSIS; TETRAHYDRO-1,2-OXAZINES; AMINOCATALYSIS; STEREOCENTERS; HETEROCYCLES; ALKYLATION;
D O I：
10.1021/jo201301p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly substituted tetrahydroimidazopyrimidine derivatives with three chiral centers have been synthesized for the first time using an organocatalytic asymmetric domino aza-Michael Mannich reaction of alpha,beta-unsaturated aldehydes and N-arylidene-1H-imidazol-2-amines. This efficient approach furnishes the products in good yields (42-87%) with excellent stereoselectivities (>20:1 dr, up to >99% ee).
引用
收藏
页码：8064 / 8069
页数：6
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