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

Qing Li; Chang-Hua Ding; Xiao-Hui Li; Walter Weissensteiner; Xue-Long Hou

doi:10.1055/s-0031-1289653

PAPER

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

Qing Li^a, Chang-Hua Ding^a, Xiao-Hui Li^b, Walter Weissensteiner^c, 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

Abstract

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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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References

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