title: Coumarins from free ortho-hydroxy cinnamates by Heck-Matsuda arylations: a scalable total synthesis of (R)-tolterodine.
abstract: Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.
authors.affiliation: Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, CEP. 13084-971, Campinas, São Paulo, Brazil.
authors.forename: Daniela A
authors.initials: DA
authors.lastname: Barancelli
authors.forename: Airton G
authors.initials: AG
authors.lastname: Salles
authors.forename: Jason G
authors.initials: JG
authors.lastname: Taylor
authors.forename: Carlos Roque D
authors.initials: CR
authors.lastname: Correia
mesh_terms: D001559:Benzhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003408:Cresols / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010665:Phenylpropanolamine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000068737:Tolterodine Tartrate
chemical_list: D001559:Benzhydryl Compounds; D002934:Cinnamates; D003374:Coumarins; D003408:Cresols; D004952:Esters; D010665:Phenylpropanolamine; D000068737:Tolterodine Tartrate; D010165:Palladium