Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

被引：48

作者：

Chauhan, Pankaj ^{[1
]}

Mahajan, Suruchi ^{[1
]}

Raabe, Gerhard ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 12期

基金：

欧洲研究理事会;

关键词：

TRICYCLIC CARBON FRAMEWORKS; DOMINO REACTIONS; MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; FUNCTIONALIZED CYCLOHEXANES; 1,6-MICHAEL ADDITION; STEREOGENIC CENTERS; CASCADE REACTIONS; IBOTENIC ACID; ALPHA;

D O I：

10.1039/c4cc09730k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between beta-dicarbonyl compounds, beta-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.

引用

页码：2270 / 2272

页数：3

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