Amide Group Directed Protonolysis of Cyclopropane. An Approach to 2,2-Disubstituted Pyrrolidines

17th Blue Danube Symposium on Heterocyclic Chemistry: Abstract Book 2017
Marija Skvorcova, Aigars Jirgensons

We have shown that the regioselective protonolytic C −C bond cleavage of acylated aminomethyl cyclopropanes 1 can be achieved using trifluoroacetic acid. The intermediate tertiary carbenium ion 2 undergoes intramolecular amination to give 2,2 -disubstituted pyrrolidines 3 in very good yields (more than 10 examples, yield up to 99 %)

Keywords
pyrrolidine, protonolysis, protonated amide

Skvorcova, M., Jirgensons, A. Amide Group Directed Protonolysis of Cyclopropane. An Approach to 2,2-Disubstituted Pyrrolidines. In: 17th Blue Danube Symposium on Heterocyclic Chemistry: Abstract Book, Austria, Linz, 30 Aug-2 Sep., 2017. Linz: Johannes Kepler University, 2017, pp.118-118.

Publication language
English (en)