Enantioselective [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Trifluoromethylated 2-Butenedioic Acid Diesters

被引：36

作者：

Du, Dan ^{[1
,2
]}

Jiang, Yu ^{[1
,2
]}

Xu, Qin ^{[1
,2
]}

Tang, Xiang-Ying ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMCATCHEM | 2015年 / 7卷 / 08期

基金：

中国国家自然科学基金;

关键词：

cycloaddition; fluorine; organocatalysis; quaternary carbon stereocenter; spiro compounds; HIGHLY EFFICIENT; ASYMMETRIC-SYNTHESIS; SPIROCYCLOPENTANE BIOXINDOLES; MICHAEL ADDITION/CYCLIZATION; ALLYLIC TRIFLUOROMETHYLATION; SPIROOXINDOLE DERIVATIVES; ALDOL REACTIONS; CONSTRUCTION; QUATERNARY; CARBON;

D O I：

10.1002/cctc.201500141

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The highly efficient organocatalytic enantioselective [3+2] cyclization of 3-isothiocyanato oxindoles with trifluoromethylated 2-butenedioic acid diesters for the synthesis of spirooxindoles possessing a CF3-containing quaternary carbon stereocenter was explored. An enantiodivergent approach for the synthesis of spirooxindoles by regulation of the temperature was demonstrated at different temperatures. The outcome of the reaction featured high diastereo- and enantioselectivities. Several interesting enantioenriched spirooxindole derivatives bearing a trifluoromethyl quaternary carbon stereocenter were synthesized from the products of this reaction.

引用

页码：1366 / 1371

页数：6

共 118 条

[1] Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].