Synthesis of Enantiomerically Pure α-Substituted Propargylic Amines by Reaction of Organoaluminum Reagents with Oxazolidines

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane−triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.