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Synfacts 2007(4): 0388-0388
DOI: 10.1055/s-2007-968357
DOI: 10.1055/s-2007-968357
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Fluorination of tert-Butoxycarbonyl Lactones and Lactams
T. Suzuki, T. Goto, Y. Hamashima, M. Sodeoka*
RIKEN, Saitama, Japan
Further Information
Publication History
Publication Date:
23 March 2007 (online)
Significance
The authors describe the enantioselective fluorination of lactones and lactams. They extend their use of the bisphosphine-Pd-water complexes to generate the proposed chiral enolate. The use of 2,6-lutidine as a co-activator was necessary for the less-acidic lactams. The use of alcoholic solvents was necessary as reactions performed in normal organic solvents were extremely slow. Both five- and six-membered lactones and lactams work well in this reaction giving products with >90% ee.