title: Regiochemical switching of Mitsunobu cyclisation mode of vicinal diamines with pendant hydroxyl group.
abstract: Ambident 1,2-diamines derived from the nitro-Mannich reaction containing both a tosyl amide and a secondary amine could be regioselectively cyclised through the tosyl amide onto a pendant primary hydroxyl group to give piperazine (60-75% yields) or 1,4-diazepane (71% yield) ring systems under Mitsunobu conditions. For some substrates addition of Et(3)N.HCl encouraged regioselective cyclisation through the secondary amine leading to aziridine ring systems.
authors.affiliation: School of Chemistry, University of Nottingham, Nottingham, UK. j.anderson@nottingham.ac.uk
authors.forename: James C
authors.initials: JC
authors.lastname: Anderson
authors.forename: Helen A
authors.initials: HA
authors.lastname: Chapman