Pyrrolidine Derivatives via Protolytic Cleavage of Cyclopropane C-C Bond

15th Belgian Organic Synthesis Symposium: Programme & Book of Abstracts 2016
Marija Skvorcova, Aigars Jirgensons

Ring opening of cyclopropanes provides an unusual option for the functionalization of C-C bond. In literature, it is known that the cleavage of cyclopropane can be promoted by electrophiles such as Hg2+, Pt2+, Tl2+, Pd2+, Br+, H+, however, regioselectivity for the attack of the electrophile is difficult to achieve. Herein we present directed protolytic cleavage of cyclopropane where protonated amide serves as an intramolecular proton donor. An efficient rote to pyrrolidine derivatives.

Keywords
pyrrolidine, amides, protonolysis, cyclopropane

Skvorcova, M., Jirgensons, A. Pyrrolidine Derivatives via Protolytic Cleavage of Cyclopropane C-C Bond. In: 15th Belgian Organic Synthesis Symposium: Programme & Book of Abstracts, Belgium, Antwerp, 10-15 July, 2016. Antwerp: 2016, pp.336-336.

Publication language
English (en)