title: Rhodium(II)-Catalyzed Isomerization of Cyclopropenylmethyl Esters into (Acyloxymethylene)cyclopropanes.
abstract: In the presence of a rhodium(II) catalyst, 3,3-disubstituted cyclopropenylmethyl esters that possess an electron-rich or neutral aromatic group undergo isomerization into (acyloxymethylene)cyclopropanes. This transformation, which proceeds with inversion of configuration at the stereogenic center, complements the previously disclosed rearrangement reactions of cyclopropenylmethyl esters. The products arising from this new rhodium-catalyzed rearrangement contain an enol ester group that can be subsequently functionalized to access stereodefined arylcyclopropanes.
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology, and Innovation (CBI), ESPCI Paris, CNRS (UMR 8231), PSL Research University, 10 rue Vauquelin, 75231, Paris Cedex 05, France.
authors.forename: Alexis
authors.initials: A
authors.lastname: Archambeau
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology, and Innovation (CBI), ESPCI Paris, CNRS (UMR 8231), PSL Research University, 10 rue Vauquelin, 75231, Paris Cedex 05, France.
authors.forename: Dinh-Vu
authors.initials: DV
authors.lastname: Nguyen
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology, and Innovation (CBI), ESPCI Paris, CNRS (UMR 8231), PSL Research University, 10 rue Vauquelin, 75231, Paris Cedex 05, France. christophe.meyer@espci.fr.
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology, and Innovation (CBI), ESPCI Paris, CNRS (UMR 8231), PSL Research University, 10 rue Vauquelin, 75231, Paris Cedex 05, France. janine.cossy@espci.fr.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
keywords: alkylidenecyclopropanes; cyclopropenes; rearrangement; rhodium; strained molecules