Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride
journal contributionposted on 17.09.2010, 00:00 by Purba Mukerjee, Mohammed Abid, Frank C. Schroeder
We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H2O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).