Direct vinylation and ethynylation of nitrones. Stereodivergent synthesis of allyl and propargyl amines

Article abstract of DOI:10.1016/0957-4166(96)00222-4

The addition of vinyl and ethynyl organometallic reagents to the nitrone derived from D-glyceraldehyde affords allyl and propargyl hydroxylamines which are easily converted into the corresponding allyl and propargyl amines. The stereoselectivity of the addition step can be controlled by the presence (or absence) of diethyl aluminium chloride.