Rhodium(II)-Catalyzed Isomerization of Cyclopropenylmethyl Esters into (Acyloxymethylene)cyclopropanes

Alexis Archambeau; Dinh-Vu Nguyen; Christophe Meyer; Janine Cossy

doi:10.1002/chem.201505063

Rhodium(II)-Catalyzed Isomerization of Cyclopropenylmethyl Esters into (Acyloxymethylene)cyclopropanes

Chemistry. 2016 Apr 18;22(17):6100-10. doi: 10.1002/chem.201505063. Epub 2016 Mar 15.

Authors

Alexis Archambeau¹, Dinh-Vu Nguyen¹, Christophe Meyer², Janine Cossy³

Affiliations

¹ 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.
² 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.
³ 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.

PMID: 26990014
DOI: 10.1002/chem.201505063

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.

Keywords: alkylidenecyclopropanes; cyclopropenes; rearrangement; rhodium; strained molecules.

Publication types

Research Support, Non-U.S. Gov't