title: Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis.
abstract: Rhodium catalysed hydrogenation of 3-methylene-1,2-diazetidines with a range of chiral ligands is reported. Using Mandyphos, excellent levels of chemo- and enantioselectivity (up to 89% ee) can be achieved. Reductive cleavage of the derived 3-substituted 1,2-diazetidine with LiDBB provides the enantioenriched biscarbamate protected 1,2-diamine.
authors.affiliation: Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK.
authors.forename: Greg P
authors.initials: GP
authors.lastname: Iacobini
authors.forename: David W
authors.initials: DW
authors.lastname: Porter
authors.forename: Michael
authors.initials: M
authors.lastname: Shipman
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001384:Azetidines; D003959:Diamines; D012238:Rhodium