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Synthesis 2009(9): 1525-1530  
DOI: 10.1055/s-0028-1088124
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© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Enantioselective Conjugate Addition of 2-Fluoromalonate to Nitroolefins: Direct Synthesis of Chiral Fluorinated γ-Nitro Carboxylic Acid Derivatives

Hao Li, Liansuo Zu, Hexin Xie, Wei Wang*
Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA
Fax: +1(505)2772609; e-Mail: wwang@unm.edu;
Further Information

Publication History

Received 29 January 2009
Publication Date:
14 April 2009 (online)

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Abstract

An unprecedented organocatalytic asymmetric Michael addition of fluorine-containing carbon-centered nucleophiles to nitroolefins has been described. The process features the creation of a fluorine-containing quaternary carbon center and an adjacent chiral carbon center adducts with good to excellent level of enantioselectivity.

Key words

cinchona alkaloid - conjugate addition - fluorination - nitroolefin

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CCDC-716267 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk.