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Synlett 1991; 1991(6): 415-417
DOI: 10.1055/s-1991-20747
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Use of Phenylsulphonylmethano Ethers in Synthesis: A New Versatile Route to Substituted Cyclic Ethers

Philippe Charreau* , Steven V. Ley, Thomas M. Vettiger, Sadie Vile
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England
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Publication Date:
07 March 2002 (online)

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Alkylation of the anion generated from [(benzyloxy)methylsulphonyl]benzene 1 with tetrahydropyranyl-protected bromo alcohols gives intermediates 2-8 [1-benzyloxy-ω-(tetrahydropyran-2-yloxy)alkyl phenyl sulphones]. Deprotection and intramolecular cyclisation using sodium hydrogen carbonate and diethyl ether-magnesium bromide complex in tetrahydrofuran affords benzyl-protected lactols with ring sizes ranging from five to eight.

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