Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds.
[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.
Shintani
Ryo
R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Ueyama
Kazuhito
K
Yamada
Ichiro
I
Hayashi
Tamio
T
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*
D001897:Boronic Acids; D005650:Fumarates; D008024:Ligands; D008298:Maleates; D009636:Norbornanes; D012238:Rhodium