Stereospecific Copper-Catalyzed Domino Ring Opening and sp³ C-H Functionalization of Activated Aziridines with N-Alkylanilines

Mani Sengoden, Abhisikta Bhowmick and Tharmalingam Punniyamurthy*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, Email: tpunniiitg.ernet.in

M. Sengoden, A. Bhowmick, T. Punniyamurthy, Org. Lett., 2017, 19, 158-161.

DOI: 10.1021/acs.orglett.6b03458

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Abstract

Copper efficiently catalyzes a reaction of N-sulfonylaziridines and N-alkylanilines in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines via nucleophilic ring opening, sp³ C-H functionalization, and C-N bond formation. The protocol can be used for the enantiospecific synthesis of imidazolidines with excellent optical purity.

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proposed mechanism

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"On Water" C(sp³)-H Functionalization/C-O/C-N Bonds Formations: Synthesis of Functionalized Oxazolidines and Imidazolidines

V. Satheesh, M. Sengoden, T. Punniyamurthy, J. Org. Chem., 2016, 81, 9792-9801.

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Key Words

imidazolidines, TBHP

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ID: J54-Y2017