Synlett 1997; 1997(11): 1285-1286
DOI: 10.1055/s-1997-1017
© 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.

A New Route to Substituted Dihydropyrans

G. L. Edwards* , D. J. Sinclair, C. D. Wasiowych
  • *School of Chemistry, University of New South Wales, Syndney, N.S.W., 2052, Australia, FAX: (+) 61 2 9385 6141, E-mail:
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Deprotonation and subsequent alkylation of 3,4-dihydro-6-(para-toluenesulfonylmethyl)-2H-pyran gives monoalkylated products in good yields, with excellent α selectivity. The alkylation succeeds not only for reactive haloalkanes, but also for simple primary and secondary alkyl bromides. Desulfonylation with sodium amalgam provides a new and simple route to substituted dihydropyrans.