title: Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates.
abstract: We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China. mshi@mail.sioc.ac.cn.
authors.forename: Sabilla
authors.initials: S
authors.lastname: Zhong
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.forename: Angela
authors.initials: A
authors.lastname: Bihlmeier
authors.forename: Min
authors.initials: M
authors.lastname: Shi
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002942:Circular Dichroism; D007097:Imines / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
chemical_list: D000596:Amino Acids; D007097:Imines; D026121:Indole Alkaloids; D010756:Phosphoric Acids; D010880:Piperidines; C032727:piperidine; C030242:phosphoric acid; D013890:Thiourea