title: Intramolecular Nucleophilic Deselenenylation Reactions Promoted by Benzeneselenenyl Triflate. Stereospecific Synthesis of Vicinal Amino Alcohol Precursors.
abstract: After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides, containing internal oxygen or nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and oxazolidin-2-ones has been developed.
authors.affiliation: Istituto di Chimica Organica, Facoltà di Farmacia, Università di Perugia, 06100 - Perugia, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Tingoli
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Testaferri
authors.forename: Andrea
authors.initials: A
authors.lastname: Temperini
authors.forename: Marcello
authors.initials: M
authors.lastname: Tiecco