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Synlett 1997; 1997(11): 1285-1286
DOI: 10.1055/s-1997-1017
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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: g.edwards@unsw.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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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.

free radicals - sulfones - dihydropyrans - alkylation - desulfonylation