Synlett 1991; 1991(5): 321-323
DOI: 10.1055/s-1991-34734
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
07 March 2002 (online)

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.