Highly α-selective hydrolysis of α,β-epoxyalcohols using tetrabutylammonium fluoride.
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/H(2)O 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).
Mukerjee
Purba
P
Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
Abid
Mohammed
M
Schroeder
Frank C
FC
D000438:Alcohols / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000438:Alcohols; D001688:Biological Products; D004852:Epoxy Compounds; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium