AI Article Synopsis
- A new inexpensive method using a Zn-AcOH system has been developed for selectively opening donor-acceptor cyclopropanes.
- This method efficiently reduces various types of cyclopropanes, particularly those with 2-(het)aryl groups, allowing for easy access to important chemical compounds.
- The resulting compounds can be transformed into useful products, including pharmacologically significant molecules like carbazoles and δ-lactams.
Article Abstract
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).
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