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

页码：8064 / 8069

页数：6

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