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Updated: Aug 15, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
A Widely Applicable and Versatile Method for the Ring-Opening 1,3-Carbocarbonation of Donor-Acceptor Cyclopropanes
Heinrich F von Köller1, Peter G Jones2, Daniel B Werz1
1Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstraße 21, 79104, Freiburg im Breisgau, Germany.
Abstract:
A 1,3-carbocarbonation of 2-substituted cyclopropane 1,1-dicarboxylates introduces various saturated or unsaturated carbon residues at the 1- and 3- position of the former three-membered ring. Under copper catalysis, ring-opening attack with a Grignard reagent proceeded smoothly; the intermediate was converted to the final product by reaction with appropriate carbon-based electrophiles under basic conditions. As nucleophiles, Grignard reagents derived from sp3 -, sp2 -, and sp-hybridized carbon residues were successfully employed, whereas various aliphatic bromides and EBX derivatives (for sp moieties) served as electrophiles.
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