Asymmetric Addition of Terminal Alkynes to N-(Diphenylphosphinoyl)imines Promoted by Stoichiometric Amounts of a Proline-Derived beta-Amino Alcohol

A new synthetic methodology for the preparation of optically active propargylamines is described. The alkynylation of aromatic, heteroaromatic, aliphatic and α,β-unsaturated N-(diphenylphosphinoyl) imines was investigated by using diethylzinc and a proline-derived β-amino alcohol. N-(Diphenyl-phosphinoyl)-protected propargylic amines can be synthesized in high yields and with good to excellent enantioselectivities.