A one-pot aza-Payne rearrangement-epoxide ring opening reaction of 2-aziridinemethanols: A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols

Article abstract of DOI:10.1016/0040-4039(95)01203-T

A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols via a one-pot aza-Payne rearrangement-epoxide ring opening reaction of 2-aziridinemethanols is reported. Satisfactory yields are obtained in excellent diastereoisomeric excesses by successive exposure of 2-aziridinemethanols to potassium hydride and nucleophilic reagents in a one-pot manner.