Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids <i>via</i> Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety

Abstract

)-TethTsDpen-RuCl] complex-catalyzed hydrogenation of pTIMs provided direct access to chiral primary trifluoroborate-ammoniums (pTAMs). Moreover, facile synthesis of a series of structurally diverse chiral α-aminoboronic acids from chiral pTAMs was accomplished through novel, operationally simple and efficient conversion using hexamethyldisiloxane/aqueous HCl. Using no chromatography at any point, this work allowed easy access to chiral α-aminoboronic acids, as exemplified by the synthesis of optically pure anti-cancer drugs bortezomib and ixazomib.

Topics & Concepts