title: Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: a highly enantioselective pathway for accessing chiral flavanones.
abstract: Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addition of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod*, the 1,4-addition of a variety of arylboronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (China), Fax: (+86) 755-88018304.
authors.forename: Qijie
authors.initials: Q
authors.lastname: He
authors.forename: Chau Ming
authors.initials: CM
authors.lastname: So
authors.forename: Zhaoxiang
authors.initials: Z
authors.lastname: Bian
authors.forename: Tamio
authors.initials: T
authors.lastname: Hayashi
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002867:Chromones / Q000737:chemistry*; D044950:Flavanones / Q000138:chemical synthesis*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D002867:Chromones; D044950:Flavanones; D012238:Rhodium
keywords: asymmetric 1,4-addition; chiral dienes; chiral flavanones; chromones; rhodium catalysis