Enantioselective synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates

被引：89

作者：

Wang, Tianli ^{[1
]}

Hoon, Ding Long ^{[1
]}

Lu, Yixin ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 50期

关键词：

N-FLUOROAMMONIUM SALTS; 3+2 CYCLOADDITION REACTIONS; ELECTRON-DEFICIENT ALKYNES; MICHAEL ADDITION; CINCHONA ALKALOIDS; 3-SUBSTITUTED OXINDOLES; BMS-204352 MAXIPOST(TM); CONJUGATE ADDITION; CARBONYL-COMPOUNDS; MBH CARBONATES;

D O I：

10.1039/c5cc03289j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first phosphine-catalyzed enantioselective gamma-addition of 3-fluoro-oxindoles to 2,3-butadienoates has been developed. A range of 3-fluoro-substituted oxindole substrates were employed, and oxindoles containing a 3-fluoro quaternary center were constructed in high yields and with excellent enantioselectivities. The gamma-addition products could be converted readily to optically enriched 3-fluoro-3-allyl oxindole derivatives.

引用

页码：10186 / 10189

页数：4

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