1242648-11-8Relevant articles and documents
Highly α-selective hydrolysis of α,β-epoxyalcohols using tetrabutylammonium fluoride
Mukerjee, Purba,Abid, Mohammed,Schroeder, Frank C.
supporting information; experimental part, p. 3986 - 3989 (2010/11/04)
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).