Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Regioselective Hydrogenolysis of Donor–Acceptor Cyclopropanes with Zn-AcOH Reductive System
Ekaterina M. Budynina, Konstantin L. Ivanov, Mikhail Ya. Melnikov, Alexander G. Majouga, Stanislav I. Bezzubov, Gennadij V. Latyshev, Elena V. Villemson
A convenient low-cost method for regioselective ring-opening of donor–acceptor cyclopropanes with the Zn-AcOH reductive system was developed. The general character of the method was displayed via efficient reduction of a representative series of 2-(het)arylcyclopropane-1,1-diesters as well as donor–acceptor cyclopropanes with other types of electron-withdrawing activating groups. This method opens a rapid access to γ-substituted propyl-1,1-diesters, ketoesters, cyanoesters, cyanoamides, dinitriles, etc., many of which are not readily accessible with alternative methods. The utility of the synthesized compounds was demonstrated by transforming them into valuable acyclic and cyclic compounds (including pharmacologically relevant carbazoles, δ-lactams, and oxindole derivatives).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01549

DOI: 10.1021/acs.joc.7b01549

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