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

页码：759 / 761

页数：3

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