Dispiroketals in Synthesis (Part 22)1: Use of Chiral 2,2’-Bis(phenylthiomethyl)dihydropyrans as New Protecting and Resolving Agents for 1,2-Diols

Abstract

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.