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Synthesis 2012(2): 265-271
DOI: 10.1055/s-0031-1289653
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
Weitere Informationen
Received
21 September 2011
Publikationsdatum:
22. Dezember 2011 (online)
Publikationsverlauf
Publikationsdatum:
22. Dezember 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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