title: Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds.
abstract: [reaction: see text] A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
authors.forename: Ryo
authors.initials: R
authors.lastname: Shintani
authors.forename: Kazuhito
authors.initials: K
authors.lastname: Ueyama
authors.forename: Ichiro
authors.initials: I
authors.lastname: Yamada
authors.forename: Tamio
authors.initials: T
authors.lastname: Hayashi
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D005650:Fumarates / Q000138:chemical synthesis*; D008024:Ligands; D008298:Maleates / Q000138:chemical synthesis*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D005650:Fumarates; D008024:Ligands; D008298:Maleates; D009636:Norbornanes; D012238:Rhodium