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Regioselective Oxo-Amination of Alkenes and Enol Ethers with N-Bromosuccinimide-Dimethyl Sulfoxide Combination: A Facile Synthesis of α-Amino-Ketones and Esters

Pragati K. Prasad, Rambabu N. Reddi and Arumugam Sudalai*

*Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune, 411008, India, Email: a.sudalaincl.res.in

P. K. Prasad, R. N. Reddi, A. Sudalai, Org. Lett., 2016, 18, 500-503.

DOI: 10.1021/acs.orglett.5b03540 (free Supporting Information)


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Abstract

An oxo-amination process with readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant provides amino alcohols in a single step. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.

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Key Words

α-amination, imides, carbonyl derivatives, DMSO


ID: J54-Y2016