Highly enantioselective conjugate addition of fluoromalonates to nitroalkenes using bifunctional organocatalysts

被引：59
|
作者：
Kwon, Bo Kyung [1 ]
Kim, Sun Mi [1 ]
Kim, Dae Young [1 ]
机构：
[1] Soonchunhyang Univ, Dept Chem, Asan 336745, Chungnam, South Korea
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2009年 / 130卷 / 08期
关键词：
Bifunctional organocatalysts; Michael reaction; Nitroalkenes; Asymmetric reactions; Fluoromalonates; ASYMMETRIC MICHAEL ADDITION; ELECTROPHILIC ALPHA-AMINATION; BETA-KETO-ESTERS; QUATERNARY STEREOCENTERS; 1,3-DICARBONYL COMPOUNDS; MEDICINAL CHEMISTRY; FLUORINATION; CATALYSIS; EFFICIENT; 2,4-PENTANDIONE;
D O I：
10.1016/j.jfluchem.2009.06.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The enantioselective conjugate addition of fluoromalonates to aromatic nitroalkenes catalyzed by chiral amine-thiourea bifunctional organocatalysts generated a stereocenter at the carbon bearing the aromatic group and an adjacent prochiral center from the fluoromalonate. Treatment of fluoromalonates with aromatic nitroalkenes under mild reaction conditions afforded the corresponding 2-fluoro-2-(2-nitro-1-arylethyl)malonates with high yields (72-93%) and excellent enantioselectivities (91-98% ee). (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：759 / 761
页数：3
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