title: Copper-Catalyzed Formation of α-Alkoxycycloalkenones from N-Tosylhydrazones.
abstract: The combination of 20 mol % of copper iodide and lithium tert-butoxide triggers the formation of a broad range of substituted, functionalized α-alkoxy 2H-naphthalenones from readily available N-tosylhydrazones. The data suggests that this transformation occurs through cycloaddition of a copper carbenoid with an ester, followed by a Lewis acid-catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 (USA) http://www2.chem.uic.edu/driver.
authors.forename: Naijing
authors.initials: N
authors.lastname: Su
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 (USA) http://www2.chem.uic.edu/driver.
authors.forename: Juliana A
authors.initials: JA
authors.lastname: Theorell
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 (USA) http://www2.chem.uic.edu/driver.
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 (USA) http://www2.chem.uic.edu/driver. tgd@uic.edu.
authors.forename: Tom G
authors.initials: TG
authors.lastname: Driver
keywords: carbenes; copper; cyclizations; hydrazones; synthetic methods