title: Rh(I)-catalyzed asymmetric synthesis of 3-substituted isoindolinones through CO gas-free aminocarbonylation.
abstract: A highly efficient and accessible synthesis of chiral 3-substituted isoindolinone frameworks is described. The synthesis involved the Rh(I)-catalyzed asymmetric arylation of boronic acids to 2-halobenzaldimines and the subsequent Rh(I)-catalyzed intramolecular aminocarbonylation of the resulting 2-halobenzylamines using an aldehyde as the carbonyl source. The method tolerates a variety of functional groups, yielding isoindolinone derivatives in moderate to high yields with high ee-values. In addition, two Rh(I)-catalyzed transformations could be efficiently accomplished in a one-pot sequence to give chiral isoindolinones by the simple addition of a ligand and an aldehyde after the Rh(I)-catalyzed asymmetric arylation.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara 630-0192, Japan.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Fujioka
authors.forename: Tsumoru
authors.initials: T
authors.lastname: Morimoto
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tsumagari
authors.forename: Hiroki
authors.initials: H
authors.lastname: Tanimoto
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Nishiyama
authors.forename: Kiyomi
authors.initials: K
authors.lastname: Kakiuchi
mesh_terms: D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D005740:Gases / Q000737:chemistry*; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005740:Gases; C110621:Isoindol-1-one; D054833:Isoindoles; D002248:Carbon Monoxide; D012238:Rhodium