Amination of Carbenium Ions Generated by Directed Protonolysis of Cyclopropane

Journal of Organic Chemistry 2019
Marija Skvorcova, Tomass Lūkass Lukaševics, Aigars Jirgensons

Directed intramolecular protonolyis of the cyclopropane C-C bond is demonstrated as a strategy to generate carbenium ions. This intermediate can be subjected to amination with nitriles under Ritter reaction conditions. Directing groups such as carbamate, carboxamide, urea, ester, and ketone were found to be efficient for regioselective anti-Markovnikov cleavage of cyclopropane. Depending on the directing group, the amination provided orthogonally protected 1,4-diamine, ϵ-amino carboxylic, and ϵ-amino ketone derivatives.

DOI
10.1021/acs.joc.8b02576
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.joc.8b02576

Skvorcova, M., Lukaševics, T., Jirgensons, A. Amination of Carbenium Ions Generated by Directed Protonolysis of Cyclopropane. Journal of Organic Chemistry, 2019, Vol. 84, No. 7, pp.3780-3792. ISSN 0022-3263. Available from: doi:10.1021/acs.joc.8b02576

Publication language
English (en)