title: Synthesis of lactams by isomerization of oxindoles substituted at C-3 by an ω-amino chain.
abstract: Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by ω-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (30-96%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams α-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.
authors.affiliation: Chimie et photonique moléculaires, Institut des Sciences Chimiques de Rennes, Université de Rennes 1 , CNRS-UMR 6226, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Daad
authors.initials: D
authors.lastname: Sarraf
authors.forename: Nicolas
authors.initials: N
authors.lastname: Richy
authors.forename: Joëlle
authors.initials: J
authors.lastname: Vidal
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles
chemical_list: D000814:Aniline Compounds; D007211:Indoles; D007769:Lactams; D000078183:Oxindoles; C022960:2-oxindole