Copper–hydride catalyzed diastereo- and enantioselective synthesis of homopropargyl amines through reductive coupling of 1,3-enynes with imines

Abstract

Enantioselective synthesis of homopropargyl amines from easily available starting materials is attractive and challenging in organic synthesis field. Herein, we reported a copper(I) hydride (Cu–H)-catalyzed reductive coupling reactions of isatin ketimines or aldimines with a broad range of 1,3-enynes bearing silyl, alkyl, aryl, heteroaryl substituents, affording a variety of homopropargyl amines in up to 98 % yield with up to >95:5 dr and >99:1 er. A single multi-functional catalyst effectively controlled the chemo-, regio-, diastereo- and enantioselectivity. Selective deprotection of the resulting enantio-enriched homopropargyl amines followed by functionalizations furnished a variety of useful building blocks.