title: Intramolecular Cyclopropanation of 1,4-Dienes through Hydroboration-Homologation: Easy Access to Bicyclo[3.1.0]hexanes.
abstract: An intramolecular cyclopropanation reaction involving B-(1-chloroalkyl)catecholborane intermediates generated from 1,4-dienes through hydroboration with catecholborane and Matteson homologation was developed. This sequential procedure leading to bicyclo[3.1.0]hexanes involves the formation of three new sigma C-C bonds at the same carbon atom. A mechanistic study supports the involvement of carbocationic intermediates.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland.
authors.forename: Gong
authors.initials: G
authors.lastname: Xu
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland. philippe.renaud@dcb.unibe.ch.
authors.forename: Philippe
authors.identifier: http://orcid.org/0000-0002-9069-7109
authors.initials: P
authors.lastname: Renaud
keywords: boronic esters; chlorides; cyclopropanation; homologation; hydroboration