Download PDF
Synlett 1997; 1997(8): 919-920
DOI: 10.1055/s-1997-948
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.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >