Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

Abstract

Unlike the corresponding aldehydes, 2-( N-methylformimino)- N, N-dialkyl-1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti. [Display omitted]