Asymmetric synthesis of α-substituted propynyl amines. Application to the preparation of a polysubstituted dihydroisoindoline framework

A new route towards the asymmetric preparation of α-substituted propynylamines has been developed. The key step involved a diastereoselective addition of diethylalkynylaluminum to oxazolidines derived from R-(−)-phenylglycinol. The use of this reaction for the rapid preparation of a polysubstituted isoindoline framework is described.