期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 14, 页码 2547-2554出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600203
关键词
Synthetic methods; Nitrogen heterocycles; Regioselectivity; Rearrangement; Difunctionalization
资金
- Indian Institute of Science (IISc)
- Council of Scientific and Industrial Research (CSIR), New Delhi
- Jawaharlal Nehru Centre Advanced Scientific Research (JNCASR)
- Department of Science and Technology (DST), New Delhi
A straightforward method is reported for the stereoselective anti-Markovnikov geminal diamination and stoichiometric geminal dioxygenation of vinylarenes mediated by a bromonium ion. The role of the substituent on the nucleophile and the nucleophilicity of the heteroatom in the competing geminal and vicinal addition pathways has been described. The stereoselectivity of the geminal dioxygenation is dependent on the ring size of the product and the position of the substituent that induces the stereoselectivity. The migration of the phenyl group through a semi-pinacol rearrangement during the geminal addition process was confirmed by the results of deuterium labelling studies.
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