title: Enantioselective assembly of spirocyclic oxindole-dihydropyranones through NHC-catalyzed cascade reaction of isatins with N-hydroxybenzotriazole esters of α,β-unsaturated carboxylic acid.
abstract: An NHC-catalyzed formal [4 + 2] reaction of isatins with N-hydroxybenzotriazole ester of α,β-unsaturated carboxylic acids bearing γ-H to construct spirocyclic oxindole-dihydropyranones featuring a chiral tetrasubstituted carbon stereogenic center was developed. The high enantioselectivity, the ready availability of the raw materials, the facile assembly, and the potential biological significance of the final products make this protocol an attractive alternative for the synthesis of spirocyclic heterocycles.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
authors.forename: Yonglei
authors.initials: Y
authors.lastname: Que
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
authors.forename: Tuanjie
authors.initials: T
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
authors.forename: Chenxia
authors.initials: C
authors.lastname: Yu
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
authors.forename: Xiang-Shan
authors.initials: XS
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
authors.forename: Changsheng
authors.initials: C
authors.lastname: Yao
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006571:Heterocyclic Compounds / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D004952:Esters; D006571:Heterocyclic Compounds; D007211:Indoles; D011753:Pyrones; D013141:Spiro Compounds; D014230:Triazoles; C030011:carbene; D007510:Isatin; D008697:Methane