One-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure4-hydroxy-4,5-dihydroisoxazole 2-oxides

[GRAPHICS] A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols i nto enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has bee n found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separ ated as such or as the bis-TDS ethers, A preliminary example of reductive c leavage of 1 to the corresponding amino polyol is also reported.