title: Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.
abstract: The cationic gold phosphine complex [{PCy2 (o-biphenyl)}Au(NCMe)](+) SbF6 (-) (Cy=cyclohexyl) catalyzes the intermolecular, anti-Markovnikov hydroamination reaction of monosubstituted and cis- and trans-disubstituted alkylidenecyclopropanes (ACPs) with imidazolidin-2-ones and other nucleophiles. This reaction forms 1-cyclopropyl alkylamine derivatives in high yield and with high regio- and diastereoselectivity. NMR spectroscopic analysis of gold π-ACP complexes and control experiments point to the sp hybridization of the ACP internal alkene carbon atom as controlling the regiochemistry of the ACP hydroamination reaction.
authors.affiliation: French Family Science Center, Duke University, Durham, NC 27708-0346 (USA).
authors.forename: Jacob C
authors.initials: JC
authors.lastname: Timmerman
authors.forename: Bradley D
authors.initials: BD
authors.lastname: Robertson
authors.forename: Ross A
authors.initials: RA
authors.lastname: Widenhoefer
keywords: cyclopropanes; gold; homogeneous catalysis; hydroamination; reaction mechanisms