title: Interrupting the Nazarov Cyclization with Bromine.
abstract: The generation of dibrominated cyclopentenones via an interrupted Nazarov cyclization is reported. The installation of two bromine atoms occurs at the α and α' positions of the cyclopentenyl scaffold via successive nucleophilic and electrophilic bromination of the 2-oxidocyclopentenyl cation and its resulting enolate. Notably, the reaction proceeds with good diastereoselectivity, favoring the symmetrical product.
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada.
authors.forename: Devon J
authors.initials: DJ
authors.lastname: Schatz
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada.
authors.forename: Yonghoon
authors.initials: Y
authors.lastname: Kwon
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada.
authors.forename: Thomas W
authors.initials: TW
authors.lastname: Scully
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada.
authors.forename: F G
authors.identifier: 0000-0001-7419-2314
authors.initials: FG
authors.lastname: West