title: Highly efficient hydrogen-bonding catalysis of the Diels-Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons.
abstract: Carbazolespirooxindole derivatives were synthesized in a high-yielding, atypically rapid, stereocontrolled Diels-Alder reaction catalyzed by a C(2)-symmetric bisthiourea organocatalyst. Simple precursors and mild conditions were used to construct carbazolespirooxindole derivatives with high enantiopurity and structural diversity under H-bonding catalysis. The practical approach recycles the organocatalyst and solvent. This simple and efficient operational procedure will allow diversity-oriented syntheses of this intriguing class of compounds.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Gloria
authors.initials: G
authors.lastname: Hernández-Torres
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D002384:Catalysis; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D007211:Indoles; D013890:Thiourea