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Synfacts 2008(5): 0498-0498  
DOI: 10.1055/s-2008-1072674
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Fluorinated Cyclopentene Derivatives

Contributor(s): Mark Lautens, Frédéric Ménard
Y.-Y. Yang, J. Xu, Z.-W. You, X.-h. Xu, X.-L. Qiu, F.-L. Qing*
Shanghai Institute of Organic Chemistry and Donghua University, Shanghai, P. R. of China
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

The interest in introducing the gem-difluoromethylene group in biologically active compounds arises from important changes in physical, chemical and biological properties. The introduction of such a group into carbocyclic nucleosides has however been impeded by the lack of a suitable method allowing fluorine atom incorporation. The authors have taken advantage of the ease of esterifying allylic alcohols with chloro­difluoroacetic acid to incorporate a CF2 group in a carbocyclic structure. The products 2 obtained after Reformatsky-Claisen cascade were further elaborated to obtain the desired nucleosidic target 6.