Synthesis of 2-Unsubstituted Pyrrolidines and Piperidines from Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5-Triazinanes as Surrogates for Formylimines

Lennart K. B. Garve, Alexander Kreft, Peter G. Jones and Daniel B. Werz*

*Institute for Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany, Email: d.werztu-braunschweig.de

L. K. B. Garve, A. Kreft, P. G. Jones, D. B. Werz, J. Org. Chem., 2017, 82, 9235-9242.

DOI: 10.1021/acs.joc.7b01631

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Abstract

In the presence of MgI₂ as Lewis acid, donor-acceptor cyclopropanes or corresponding cyclobutanes react with 1,3,5-triazinanes, leading to the 2-unsubstituted pyrrolidines and piperidines under mild conditions in good yields. This protocol tolerates various functional groups and provides an efficient entry to pyrrolidines and piperidines.

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proposed mechanism

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Key Words

pyrrolidines

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ID: J42-Y2017