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Synthesis 2012(2): 265-271  
DOI: 10.1055/s-0031-1289653
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereo- and Enantioselective Synthesis of Fluorinated Proline Derivatives via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition

Qing Lia, Chang-Hua Dinga, Xiao-Hui Lib, Walter Weissensteinerc, Xue-Long Hou*a,b
a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)54925100; e-Mail: xlhou@sioc.ac.cn;
b Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
c Faculty of Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Vienna, Austria
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Publication History

Received 21 September 2011
Publication Date:
22 December 2011 (online)

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Abstract

A catalytic asymmetric cycloaddition reaction of fluoromethyl-substituted nitroalkenes with azomethine ylides was developed using a catalyst derived from copper(I) perchlorate and a commercially available, chiral Walphos ligand. This method provides a simple approach to optically active exo-3-(fluoromethyl)proline derivatives in high yields, as well as in high diastereo- and enantioselectivities.

Key words

1,3-dipolar cycloaddition - copper - asymmetric catalysis - azomethine ylides - fluorinated prolines

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