title: Enantioselective synthesis of dihydro-1H-benzindoles.
abstract: The first examples of dihydro-1H-benzindoles by enantioselective γ-lactamization reaction of naphthyl sulfilimines with trichloroacetyl chloride in the presence of ZnCu as catalyst (≥98:2 er and 65-80% yields) are described. Products are obtained by [3,3]-sigmatropic rearrangement of the azasulfonium enolate or followed by a second allylic rearrangement that transfers chirality. The absolute stereochemistry was confirmed by X-ray crystallography, which provides support for the mechanisms proposed.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA. gustavo.silveira@iq.ufrgs.br
authors.forename: Gustavo P
authors.initials: GP
authors.lastname: Silveira
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Marino
mesh_terms: D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D062845:Chloroacetates; D007211:Indoles; D003300:Copper; C037540:trichloroacetyl chloride; D015032:Zinc