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Synfacts 2007(7): 0723-0723
DOI: 10.1055/s-2007-968670
DOI: 10.1055/s-2007-968670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Iridium-Catalyzed Asymmetric Hydrogenation of Fluorinated Olefins
M. Engman, J. S. Diesen, A. Paptchikhine, P. G. Andersson*
Uppsala Universitet, Sweden
Further Information
Publication History
Publication Date:
22 June 2007 (online)
Significance
The authors report the first successful asymmetric hydrogenation of vinyl fluorides. The current method provides access to compounds bearing CHF stereocenters adjacent to functionalities amenable to synthetic transformation. A major difficulty encountered was the undesired defluorination of substrate under the reaction conditions. Of the two possible pathways, formation of 4 from 2 was ruled out experimentally, indicating that the vinylic fluorine undergoes cleavage.