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Synlett 1996; 1996(8): 791-792
DOI: 10.1055/s-1996-5522
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Dispiroketals in Synthesis (Part 22)1: Use of Chiral 2,2’-Bis(phenylthiomethyl)dihydropyrans as New Protecting and Resolving Agents for 1,2-Diols

Steven V. Ley* , Shigeru Mio, Benjamin Meseguer
  • *Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
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Publication Date:
31 December 2000 (online)

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Chiral 2,2’-bis(phenylthiomethyl)dihydropyrans can be used to enantioselectively protect a range of 1,2-diols as their corresponding dispiroketals. Following oxidation to bis-sulfone deprotection was achieved by base promoted β-elimination with lithium hexamethyldisilazide.

bisdihydropyrans - vicinal diol protection - resolution of 1,2-diols - dispiroketals

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