title: Practical Synthesis of Axially Chiral Dicarboxylates via Pd-Catalyzed External-CO-Free Carbonylation.
abstract: We have developed a safe and practical synthetic method for preparing axially chiral diphenyl dicarboxylates using Pd-catalyzed external-CO-free carbonylation with phenyl formate as a CO surrogate. Optimized conditions consisted of axially chiral [1,1'-binaphthalene]-2,2'-diyl ditriflate and its congeners, each easily prepared from commercially available enantiomerically pure diols, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane, ethyldiisopropylamine, and no solvent. To demonstrate the potential utility of these products, this method was conducted on gram-scale and the phenyl ester products were converted to other useful compounds, and both processes were carried out without difficulty.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka.
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Konishi
authors.forename: Fumika
authors.initials: F
authors.lastname: Hoshino
authors.forename: Kei
authors.initials: K
authors.lastname: Manabe
mesh_terms: D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D003998:Dicarboxylic Acids; D009942:Organometallic Compounds; D010165:Palladium; D002248:Carbon Monoxide