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Synlett 1991; 1991(5): 321-323
DOI: 10.1055/s-1991-34734
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An Enantioselective Deprotonation Route to a Versatile Intermediate for C-Nucleoside Synthesis

P. J. Cox* , N. S. Simpkins
  • *Department of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, England
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Publication Date:
07 March 2002 (online)

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The asymmetric transformation of ketone 1 (exo-cis-6,7-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3-one) into optically active silyl enol ether 2 (exo-cis-6,7-isopropylidenedioxy-3-trimethylsiloxy-8-oxabicyclo[3.2.1]oct-2-ene) in up to 85% ee was achieved using the homochiral lithium amide base 6 [lithium (R,R)-bis(1-phenylethyl)amide]. Conversion of 2 into a known key intermediate 3 (methyl 2,3-O-isopropylidene-ß-ribofuranosyl-acetate) for C-nucleoside synthesis was possible in a highly efficient two-step sequence.