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Gold-Catalyzed Diastereoselective Synthesis of α-Fluoroenones from Propargyl Acetates

M. N. Hopkinson, G. T. Giuffredi, A. D. Gee, V. Gouverneur* – 2010

A diastereoselective preparation of α-fluoroenones from propargyl acetates has been developed proceeding via a gold-catalyzed rearrangement-fluorination cascade. Control reactions are consistent with a mechanism involving a gold-mediated 3,3-sigmatropic shift followed by a direct, nongold-catalyzed electrophilic fluorination of the allenyl acetate intermediate.

Title
3. Gold-Catalyzed Diastereoselective Synthesis of α-Fluoroenones from Propargyl Acetates
Author
M. N. Hopkinson, G. T. Giuffredi, A. D. Gee, V. Gouverneur*
Publisher
Synlett
Date
2010
Identifier
DOI: 10.1055/s-0030-1258992
Source(s)
Citation
Synlett 2010, 2737-2742