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

Marija Skvorcova and Aigars Jirgensons*

*Latvian Institute of Organic Synthesis, Riga LV-1006, Latvia, Email: aigarsosi.lv

M. Skvorcova, A. Jirgensons, Org. Lett., 2017, 19, 2478-2481.

DOI: 10.1021/acs.orglett.7b00584 (free Supporting Information)



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Abstract

Regioselective protonolytic C-C bond cleavage of acylated aminomethyl cyclopropanes can be achieved using trifluoroacetic acid to provide 2,2-substituted pyrrolidines via an intermediate tertiary carbenium ion. The strength of the acid and the amine substituent are important factors to achieve high regioselectivity, suggesting intramolecular proton transfer from the protonated amide function.

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Key Words

Pyrrolidines


ID: J54-Y2017