title: Dinuclear zinc catalyzed asymmetric spirannulation reaction: an umpolung strategy for formation of α-alkylated-α-hydroxyoxindoles.
abstract: A highly diastereo- and enantioselective formal [3 + 2] cycloaddition of α,β-unsaturated esters and 3-hydroxyoxindoles catalyzed by a dinuclear zinc-ProPhenol complex is reported. The stereoselective Michael additions of 3-hydroxyoxindoles and the subsequent transesterifications afford spirocyclic δ-lactones.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Keiichi
authors.initials: K
authors.lastname: Hirano
mesh_terms: D000478:Alkylation; D002384:Catalysis; D004952:Esters; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D004952:Esters; D007211:Indoles; D007783:Lactones; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D015032:Zinc