Development of an enantioselective organocatalytic intramolecular cyclopropanation reaction

ORGN 266

Matthew J. Gaunt, mjg32@cam.ac.uk, Nadine Bremeyer, nb241@cam.ac.uk, and Steven V. Ley, svl1000@cam.ac.uk. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom
Catalytic processes that form functionalised cyclic molecules represent a key transformation for synthetic organic chemistry. Our recent studies have identified the utility of ammonium ylides for carbon-carbon bond formation and here we describe the development of the first enantioselective organocatalytic intramolecular cyclopropanation reaction to form [n.1.0]-bicycloalkanes. This powerful new process effects the formation of three stereocenters, two carbon-carbon bonds and two ring systems in a single transformation from linear achiral starting material.