title: Asymmetric Diels-Alder reaction of 2-methyl-3-indolylmethanols via in situ generation of o-quinodimethanes.
abstract: An asymmetric Diels-Alder reaction of 2-methyl-3-indolylmethanols and α,β-unsaturated aldehydes has been developed that relies on in situ generation of active indole-2,3-quinodimethane intermediates under mild acidic conditions and uses a secondary chiral amine as iminium activation catalyst. An array of highly enantioenriched tetrahydrocarbazoles have been efficiently produced in fair to good yields.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, China.
authors.forename: You-Cai
authors.initials: YC
authors.lastname: Xiao
authors.forename: Qing-Qing
authors.initials: QQ
authors.lastname: Zhou
authors.forename: Lin
authors.initials: L
authors.lastname: Dong
authors.forename: Tian-Yu
authors.initials: TY
authors.lastname: Liu
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002227:Carbazoles; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles