Transition-Metal-Free Stereoselective Borylation of Allenamides

Abstract

Complete stereocontrol on the transition-metal-free hydroboration of the distal double bond of allenamides could be achieved when allenamides contained acetyl substituents, which provided exclusively the Z-isomer. The consecutive Pd-catalyzed cross-coupling reaction allowed the straightforward formation of trisubstituted enamides, with total control of the stereoselectivity.

Keywords: allenamines; borylation; density functional calculations; stereoselectivity; transition-metal free.