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Synlett 1992; 1992(3): 194-196
DOI: 10.1055/s-1992-21310
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Application of Homochiral Lithium Amide Base Chemistry to a Thiane Oxide System

Paul J. Cox* , Andrew Persad, Nigel S. Simpkins
  • *Department of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, England
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Publication History

Publication Date:
08 March 2002 (online)

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Treatment of trans-4-tert-butyl(diphenyl)siloxythiane oxide (6) with a homochiral lithium amide base, followed by electrophilic quench of the so-formed sulphoxide carbanion gives optically active products [e.g., (1R,2S,4R)-4-tert-butyl(diphenyl)-siloxy-2-trimethylsilylthiane 1-oxide (8)] in up to 69% ee.

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