title: Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.
abstract: Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the gamma-position allows for a facile construction of quaternary centers. The preparation of a wide variety of gamma-aryl butenolides containing a number of functional groups is outlined. An application of this chemistry for a one-pot synthesis of a tricyclic tetrahydroisoquinolinone is demonstrated.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Alan M
authors.initials: AM
authors.lastname: Hyde
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D044005:Tetrahydroisoquinolines; D010165:Palladium; C004511:butenolide; D015107:4-Butyrolactone