Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 130, Issue 8, Pages 759-761Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2009.06.002
Keywords
Bifunctional organocatalysts; Michael reaction; Nitroalkenes; Asymmetric reactions; Fluoromalonates
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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.
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