title: Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation.
abstract: An organocatalytic asymmetric allylation of 3-indolylmethanol has been established via hydrogen-bond activating mode, which directly assembles isatin-derived 3-indolylmethanols and o-hydroxystyrenes into chiral allyl-substituted oxindoles with one all-carbon quaternary stereogenic center and one newly formed C=C bond in excellent enantioselectivity and (Z)-selectivity (up to 97% ee, >20 : 1 Z/E ratio). This transformation provides an efficient strategy for asymmetric C3-functionalization of indoles and allylation of 3-indolylmethanols with precise control of the stereoselectivity in the formation of C-C and C=C bonds.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Hong-Hao
authors.initials: HH
authors.lastname: Zhang
authors.forename: Yu-Chen
authors.initials: YC
authors.lastname: Zhang
authors.forename: Yan
authors.initials: Y
authors.lastname: Jiang
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry; D000078183:Oxindoles; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007211:Indoles; D000078183:Oxindoles; D013343:Styrenes; C022960:2-oxindole; D006859:Hydrogen; D007510:Isatin