title: Regio- and Stereocontrolled Synthesis of 3-Substituted 1,2-Diazetidines by Asymmetric Allylic Amination of Vinyl Epoxide.
abstract: Pd-catalyzed asymmetric allylic amination of rac-vinyl epoxide with unsymmetrical 1,2-hydrazines proceeds with excellent regio- and stereocontrol, which after further ring closure provides differentially protected 3-vinyl-1,2-diazetidines in good yields. The chirality at C-3 exerts stereocontrol over the nitrogen centers in the 1,2-diazetidine with all substituents orientating themselves trans to their neighbors. Efficient functionalization without rupture of the strained ring is demonstrated (e.g., by cross-metathesis), establishing the first general route to C-3-substituted 1,2-diazetidines in enantioenriched form.
authors.affiliation: Department of Chemistry, University of Warwick , Gibbet Hill Road, Coventry CV4 7AL, United Kingdom.
authors.forename: Sundaram
authors.initials: S
authors.lastname: Rajkumar
authors.affiliation: Department of Chemistry, University of Warwick , Gibbet Hill Road, Coventry CV4 7AL, United Kingdom.
authors.forename: Guy J
authors.initials: GJ
authors.lastname: Clarkson
authors.affiliation: Department of Chemistry, University of Warwick , Gibbet Hill Road, Coventry CV4 7AL, United Kingdom.
authors.forename: Michael
authors.identifier: 0000-0002-3349-5594
authors.initials: M
authors.lastname: Shipman