title: An "anti-Baldwin" 3-exo-dig cyclization: preparation of vinylidene cyclopropanes from electron-poor alkenes.
abstract: Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an SN2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic vinylidene cyclopropanes can be prepared. These products are not available by standard carbene methodology.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Campbell
authors.forename: Patrick D
authors.initials: PD
authors.lastname: Pohlhaus
authors.forename: Geanna
authors.initials: G
authors.lastname: Min
authors.forename: Kohsuke
authors.initials: K
authors.lastname: Ohmatsu
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson