Enantioselective intermolecular all-carbon [4+2] annulation via N-heterocyclic carbene organocatalysis

被引：14
|
作者：
Zhang, Guoxiang
Xu, Weici
Liu, Jian
Das, Deb Kumar
Yang, Shuang
Perveen, Saima
Zhang, Hao
Li, Xinglong
Fang, Xinqiang [1 ]
机构：
[1] Univ Chinese Acad Sci, Fujian Inst Res Struct Matter FJIRSM, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 100期
基金：
美国国家科学基金会;
关键词：
DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ACYL AZOLIUMS; CATALYZED MICHAEL ADDITION; 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS; VINYLOGOUS ALDOL; NHC CATALYSIS; BETA-LACTONES; ACTIVATION; ENALS;
D O I：
10.1039/c7cc08680f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The highly stereoselective intermolecular all-carbon [4+2] annulation between in situ generated acyclic dienolates and alpha,beta-unsaturated acyl azoliums is disclosed. The identification of 2-acyloxy-3-butenones as suitable diene precursors is the key to the success of this transformation. The corresponding highly functionalized cyclohexene products, which are inaccessible from Diels-Alder reactions, were delivered with high levels of diastereo- and enantioselectivities. A series of further transformations based on the product showed the potential of this reaction.
引用
收藏
页码：13336 / 13339
页数：4
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