title: Stereocontrolled synthesis of 1,2- and 1,3-diamine building blocks from aziridine aldehyde dimers.
abstract: 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.
authors: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
authors: Sean K
authors: SK
authors: Liew
authors: Zhi
authors: Z
authors: He
authors: Jeffrey D
authors: JD
authors: St Denis
authors: Andrei K
authors: AK
authors: Yudin