title: Palladium-catalyzed intramolecular diamination of acrylic esters using sulfamates as nitrogen source.
abstract: An intramolecular diamination of acrylates is reported using sulfamates as nitrogen sources. This reaction proceeds under palladium(II) catalysis with copper bromide as oxidant and gives rise to anti-configured 2,3-diamino carboxylates as bicyclic sulfamate derivatives. An aminobrominated intermediate within the diamination reaction was isolated that allowed to clarify the reaction mechanism and to rationalize the observed preferential product stereochemistry.
authors.affiliation: Institute of Chemical Research of Catalonia, Av. Països Catalans, 16, E-43007 Tarragona, Spain.
authors.forename: Patricia
authors.initials: P
authors.lastname: Chávez
authors.forename: Jonathan
authors.initials: J
authors.lastname: Kirsch
authors.forename: Jan
authors.initials: J
authors.lastname: Streuff
authors.forename: Kilian
authors.initials: K
authors.lastname: Muñiz
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000586:Amination; D001965:Bromides / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000179:Acrylates; D000475:Alkenes; D001965:Bromides; D002264:Carboxylic Acids; D004952:Esters; D013451:Sulfonic Acids; D010165:Palladium; D003300:Copper; C005741:sulfamic acid