title: Directed metalation of 1-ester-substituted indolizines: base/electrophile-controlled regioselective functionalization.
abstract: A variety of C-2 and C-5 difunctionalized indolizines have been prepared through the reaction of 1-ester-substituted indolizines with organometallic bases followed by a reaction with different electrophiles. Metalation takes place under mild conditions allowing the isolation of a number of difunctionalized indolizines in good yields. The regioselectivity of the reaction appears to be governed by the nature of the base and electrophile.
authors.affiliation: Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo , Av. do Café S/N, Ribeirão Preto - SP 14040-903, Brazil.
authors.forename: Mônica F Z J
authors.initials: MF
authors.lastname: Amaral
authors.forename: Amanda A
authors.initials: AA
authors.lastname: Baumgartner
authors.forename: Ricardo
authors.initials: R
authors.lastname: Vessecchi
authors.forename: Giuliano C
authors.initials: GC
authors.lastname: Clososki
mesh_terms: D002384:Catalysis; D004952:Esters; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007212:Indolizines; D009942:Organometallic Compounds; D010165:Palladium