ON THE ABSOLUTE STEREOCHEMISTRIES OF HOMOCHIRAL CYCLOADDUCTS DERIVED FROM OXYGENATED ALDOXIMES AND DIVINYL SULFONE VIA AZAPROTIO CYCLOTRANSFER

Further studies into the regiospecific tandem nitrone generation/cyclo addition reaction between chiral oxygenated aldoximes and divinyl sulp hone have shown that cycloaddition diastereoselectivity can be control led by a single stereogenic centre located alpha- to the oxime moiety. Diastereoselectivity is greatly enhanced when the alpha-stereocentre constitutes part of a ring system and the absolute stereochemistry of the major cycloadduct can be accurately predicted based upon the absol ute stereochemistry at the alpha-centre of the oxime.