Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers

Vicinal
aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde
dimers in the Petasis borono-Mannich reaction. Subsequent solvent-
and/or nucleophile-dependent ring-opening of the aziridine ring yields
functionalized 1,2- and 1,3-diamines with high regioselectivity. The
ring opening is also influenced by the substitution at the C3 position
of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.