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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

Author:
Prasad, Pragati K., Reddi, Rambabu N., Sudalai, Arumugam
Source:
Organic letters 2016 v.18 no.3 pp. 500-503
ISSN:
1523-7052
Subject:
alkenes, amino alcohols, carbonyl compounds, chemical reactions, chemical structure, dimethyl sulfoxide, enol ethers, esters, oxidants, regioselectivity, secondary amines
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.
Agid:
5792297