Synthesis of Propargylamines via a Three-Component Coupling Reaction

Significance

A variety of propargylamines can be prepared in excellent yields by a three-component coupling reaction catalyzed by gold(III)-salen complexes in water. The chiral substituents on cyclic secondary amines transferred the chirality to the newly formed sp³ carbon center. When chiral prolinol derivatives were employed as the amine component, excellent diastereoselectivity was achieved (up to 99:1). Prolinol bearing bulky diphenyl groups afforded propargylamines 5 in 83% yield with 99:1 dr. Sensitive functionalities such as esters are not tolerated. A wide range of substrates reacted with complete aldehyde conversion.