Download PDF
Synlett 1995; 1995(12): 1275-1276
DOI: 10.1055/s-1995-5245
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.

Imines as Synthetic Equivalents of Primary Amines for the Nucleophilic Trapping of Thiiranium Ion Intermediates

Duncan M. Gill, Neil A. Pegg, Christopher M. Rayner*
  • *School of Chemistry, University of Leeds, Leeds LS2 9JT, U.K., email: chrisr@chem.leeds.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The use of imines, including those derived from amino esters, as selective nucleophilic trapping agents for thiiranium ions generated in situ from 2,3-epoxy sulfides under Lewis acidic conditions, is reported. The initially formed iminium ions are readily hydrolysed by aqueous base to liberate a secondary amine, the product of overall selective monoalkylation of a primary amine.

episulfonium ion - epoxide - primary amine - monoalkylation - amino acid - iminium ion

      >