title: Assembly of spirooxindole derivatives via organocatalytic iminium-enamine cascade reactions.
abstract: The assembly of complex spirocyclopentaneoxindoles via a novel organocatalytic iminium-enamine cascade process is reported. Reactions between 3-substituted oxindoles and α,β-unsaturated aldehydes catalyzed by second generation prolinol ethers provided the desired products in high yield with excellent levels of enantioselectivity in a single step.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Klaus
authors.initials: K
authors.lastname: Albertshofer
authors.forename: Kimberly E
authors.initials: KE
authors.lastname: Anderson
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004987:Ethers; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole