Geometrically Selective Synthesis of (E)-Enamides via Radical Allylation of Alkyl Halides with α-Aminoallylic Stannanes.

The reaction of α-(carbonylamino)allylic stannanes and alkyl halides using Et3B as a radical initiator selectively afforded (E)-enamides. A radical mechanism enables the E selectivity, which is unusual in a reaction using α-aminoallylic metals. In addition, this reaction system achieved a wide degree of functional group tolerance and an efficient chiral transfer reaction.