Alkoxide activation of aminoboranes towards selective amination

Piece of the (inter)action: The interaction of alkoxides with the sp(2) Bpin (pin=pinacol) moiety in aminoboranes forms the in situ Lewis acid-base adduct [RO(-) →B(OR)2 N(R')2 ] which enables the amino moiety to react as a strong nucleophile with several electrophiles, thus providing amino alcohols, β-enamino esters, and β-hydroxy amides in a direct and remarkably selective way.