Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions

被引：131

作者：

Albertshofer, Klaus

Tan, Bin

Barbas, Carlos F., III ^{[1
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 07期

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; CATALYTIC ASYMMETRIC-SYNTHESIS; DOMINO REACTIONS; DIELS-ALDER; QUATERNARY STEREOCENTERS; MULTIPLE STEREOCENTERS; SPIROCYCLIC OXINDOLES; HIGHLY EFFICIENT; 3+2 ANNULATION; CONSTRUCTION;

D O I：

10.1021/ol300441z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel organocatalytic strategy for the synthesis of highly substituted spirocyclopentaneoxindoles was developed employing simple nitrostyrenes and 3-substituted oxindoles as starting materials. Michael-Henry cascade reactions, enabled through cinchona alkaloid organocatalysis, provided products in high yield and excellent enantioselectivity in a single step.

引用

页码：1834 / 1837

页数：4

共 54 条

[51] Organocatalysis: asymmetric cascade reactions catalysed by chiral secondary amines [J].