title: Novel [1,2]- and [2,3]-Wittig rearrangements of alpha-benzyloxy beta-CF(3)-beta-lactam enolates.
abstract: [reaction: see text] alpha-Benzyloxy alpha-CF(3)-beta-lactams are shown to offer the first examples of the enolate [1,2]- and enolate ortho-[2,3]-Wittig rearrangements which provide a unique entry to the alpha-benzyl-alpha-hydroxy lactams and the alpha-aryl-alpha-hydroxy lactams, respectively. Both products are potential precursors of new trifluoromethyl isoserines, and the latter is not accessible via the usual alkylation methodology.
authors.affiliation: BIOCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Châtenay-Malabry F-92296 Cedex, France.
authors.forename: A
authors.initials: A
authors.lastname: Garbi
authors.forename: L
authors.initials: L
authors.lastname: Allain
authors.forename: F
authors.initials: F
authors.lastname: Chorki
authors.forename: M
authors.initials: M
authors.lastname: Ourévitch
authors.forename: B
authors.initials: B
authors.lastname: Crousse
authors.forename: D
authors.initials: D
authors.lastname: Bonnet-Delpon
authors.forename: T
authors.initials: T
authors.lastname: Nakai
authors.forename: J P
authors.initials: JP
authors.lastname: Bégué
mesh_terms: D000478:Alkylation; D007202:Indicators and Reagents; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D047090:beta-Lactams