title: Regioselective Oxo-Amination of Alkenes and Enol Ethers with N-Bromosuccinimide-Dimethyl Sulfoxide Combination: A Facile Synthesis of α-Amino-Ketones and Esters.
abstract: An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S(+)-O-Br species generated by the interaction of NBS with DMSO has been proven.
authors.forename: Pragati K
authors.initials: PK
authors.lastname: Prasad
authors.forename: Rambabu N
authors.initials: RN
authors.lastname: Reddi
authors.affiliation: Chemical Engineering and Process Development Division, National Chemical Laboratory , Pashan Road, Pune, 411008, India.
authors.forename: Arumugam
authors.initials: A
authors.lastname: Sudalai
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004952:Esters; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D000605:Amino Alcohols; D004952:Esters; D004987:Ethers; D007659:Ketones; D001974:Bromosuccinimide; D004121:Dimethyl Sulfoxide