N-Heterocyclic Carbene-Catalyzed Stereoselective Cascade Reaction: Synthesis of Functionalized Tetrahydroquinolines

被引：90

作者：

Zhang, Hai-Rui ^{[1
]}

Dong, Zhen-Wen ^{[1
]}

Yang, Yu-Jie ^{[1
]}

Wang, Ping-Luan ^{[1
]}

Hui, Xin-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 18期

关键词：

DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; GAMMA-BUTYROLACTONES; NUCLEOPHILIC CARBENES; ALKYNYL ALDEHYDES; MICHAEL ADDITION; NHC-CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; TRANSFER HYDROGENATION;

D O I：

10.1021/ol4024985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first N-heterocyclic carbene-catalyzed stereoselective aza-Michael-Michael-lactonization cascade reaction of 2'-aminophenylenones and 2-bromoenals for the construction of chiral functionalized tetrahydroquinolines with three consecutive stereogenic centers has been achieved in high yields (up to 98%) with excellent diastereo- (>25:1) and enantioselectivities (up to 98.7% ee).

引用

页码：4750 / 4753

页数：4

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