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Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System

Konstantin L. Ivanov, Elena V. Villemson, Gennadij V. Latyshev, Stanislav I. Bezzubov, Alexander G. Majouga, Mikhail Ya. Melnikov and Ekaterina M. Budynina*

*Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia, Email: ekatbudkinet.chem.msu.ru

K. L. Ivanov, E. V. Villemson, G. V. Latyshev, S. I. Bezzubov, A. G. Majouga, M. Ya. Melnikov, E. M. Budynina, J. Org. Chem., 2017, 82, 9537-9549.

DOI: 10.1021/acs.joc.7b01549 (free Supporting Information)


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Abstract

The Zn-AcOH reductive system enables a regioselective and rapid ring-opening of donor-acceptor cyclopropanes. 2-(Het)Arylcyclopropane-1,1-diesters as well as donor-acceptor cyclopropanes with other types of electron-withdrawing activating groups provides γ-substituted propyl-1,1-diesters, ketoesters, cyanoesters, cyanoamides, dinitriles, etc., which are not readily accessible with alternative methods.

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proposed mechanism



Key Words

hydrogenolysis of cyclopropanes, zinc


ID: J42-Y2017