title: Brønsted acid catalyzed asymmetric diels-alder reactions: stereoselective construction of spiro[tetrahydrocarbazole-3,3'-oxindole] framework.
abstract: The chiral phosphoric acid catalyzed asymmetric Diels-Alder reactions of 2-vinylindoles with methyleneindolinones have been established, which efficiently construct the spiro[tetrahydrocarbazole-3,3'-oxindole] architecture with one quaternary and three contiguous stereogenic centers in high yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 97% ee). This reaction not only provides an efficient strategy to access enantioenriched spiro[tetrahydrocarbazole-3,3'-oxindoles] based on hydrogen-bonding activation mode but also supplies successful examples of catalytic asymmetric Diels-Alder reactions for constructing complex spiro-frameworks with optical purity.
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Man-Su
authors.initials: MS
authors.lastname: Tu
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Yin
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Meng
authors.initials: M
authors.lastname: Sun
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D010756:Phosphoric Acids / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D000078183:Oxindoles; D010756:Phosphoric Acids; D013141:Spiro Compounds; C000603253:spiro(tetrahydrocarbazole-3,3'-oxindole)