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Synlett 1997; 1997(8): 919-920
DOI: 10.1055/s-1997-948
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The Enantioselective Conversion of Three-Membered Ring Sulfoxides (Episulfoxides) into Alkenyl Sulfoxides using Chiral Lithium Amide Bases

Alexander J. Blake, Susan M. Westaway, Nigel S. Simpkins*
  • *Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK, Fax (0115) 9513564; e-mail Nigel.Simpkins@ Nottingham.ac.uk
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Publikationsdatum:
31. Dezember 2000 (online)

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A novel type of chiral lithium amide base reaction, involving the rearrangement of certain types of unsymmetrical ring-fused episulfoxides, gives alkenyl sulfoxide products in up to 88% ee. The structure of one product, including its absolute stereochemistry, was determined by X-ray crystallography, following oxidation of the sulfoxide to the corresponding alkenyl sulfone.

episulfoxide - alkenyl sulfoxide - chiral lithium amide base