A Widely Applicable and Versatile Method for the Ring-Opening 1,3-Carbocarbonation of Donor-Acceptor Cyclopropanes.
Heinrich F von KöllerPeter G JonesDaniel B WerzPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2022)
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 sp 3 -, sp 2 -, 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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