title: The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates.
abstract: Introduction of a β-electron withdrawing group to cycloalkanones allows facile C-C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.
authors.affiliation: Monash University, Clayton, 3800, Melbourne, Australia.
authors.forename: Judith
authors.initials: J
authors.lastname: Hierold
authors.forename: Tina
authors.initials: T
authors.lastname: Hsia
authors.forename: David W
authors.initials: DW
authors.lastname: Lupton