title: Catalytic Enantioselective and Regioselective [3+3] Cycloadditions Using 2-Indolylmethanols as 3 C Building Blocks.
abstract: The first catalytic asymmetric cycloaddition using 2-indolylmethanols as 3C building blocks has been established by a chiral phosphoric acid-catalyzed enantioselective and regioselective [3+3] cycloaddition of 2-indolylmethanols with azomethine ylides, which constructed biologically important tetrahydro-γ-carboline frameworks in high yields and excellent enantioselectivities (up to 83 % yield, 99:1 e.r.). This reaction not only represents the first application of 2-indolylmethanols as 3C building blocks in catalytic asymmetric cycloadditions, but also has established an abnormal regioselectivity in indolylmethanol-involved transformations.
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
authors.forename: Xiao-Xue
authors.initials: XX
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, P. R. China.
authors.forename: Hong-Hao
authors.initials: HH
authors.lastname: Zhang
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
authors.forename: Guo-Hao
authors.initials: GH
authors.lastname: Li
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
authors.forename: Ying-Ying
authors.initials: YY
authors.lastname: He
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007211:Indoles
keywords: asymmetric catalysis; azomethine ylide; cycloaddition; enantioselectivity; organocatalysis