title: Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds.
abstract: A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 Groningen, AG, The Netherlands.
authors.forename: Sureshbabu
authors.initials: S
authors.lastname: Guduguntla
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 Groningen, AG, The Netherlands.
authors.forename: Valentín
authors.initials: V
authors.lastname: Hornillos
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 Groningen, AG, The Netherlands.
authors.forename: Romain
authors.initials: R
authors.lastname: Tessier
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 Groningen, AG, The Netherlands.
authors.forename: Martín
authors.initials: M
authors.lastname: Fañanás-Mastral
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 Groningen, AG, The Netherlands.
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D000068737:Tolterodine Tartrate / Q000138:chemical synthesis
chemical_list: D000498:Allyl Compounds; D007202:Indicators and Reagents; D009942:Organometallic Compounds; C030011:carbene; D000068737:Tolterodine Tartrate; D003300:Copper; D008094:Lithium; C050431:allyl bromide; D008697:Methane