title: N-heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles.
abstract: A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and α-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).
authors.affiliation: College of Materials, Chemistry & Chemical Engineering and School of Medicine, Hangzhou Normal University, Hangzhou 310036, China.
authors.forename: Limin
authors.initials: L
authors.lastname: Yang
authors.forename: Fei
authors.initials: F
authors.lastname: Wang
authors.forename: Pei Juan
authors.initials: PJ
authors.lastname: Chua
authors.forename: Yunbo
authors.initials: Y
authors.lastname: Lv
authors.forename: Liang-Jun
authors.initials: LJ
authors.lastname: Zhong
authors.forename: Guofu
authors.initials: G
authors.lastname: Zhong
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D011753:Pyrones; C030011:carbene; D008697:Methane