Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: a facile synthesis of alpha-amino-ketones and esters
| Title | Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: a facile synthesis of alpha-amino-ketones and esters |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Prasad, PK, Reddi, RN, Sudalai, A |
| Journal | Organic Letters |
| Volume | 18 |
| Issue | 3 |
| Pagination | 500-503 |
| Date Published | FEB |
| ISSN | 1523-7060 |
| Abstract | An unprecedented conversion of alkenes and enol ethers to the corresponding a-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. |
| DOI | 10.1021/acs.orglett.5b03540 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.732 |
Divison category:
Chemical Engineering & Process Development