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
收藏
页码：10186 / 10189
页数：4
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