title: Chiral Brønsted acid-catalyzed Friedel-Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes.
abstract: We disclose herein a highly enantioselective protocol for the Brønsted acid-catalyzed addition of indoles and phenols to in situ-generated ortho-quinone methides which deliver broadly substituted diarylindolylmethanes and triarylmethanes, respectively, in a one-pot reaction under very mild conditions. A chiral phosphoric acid catalyst has been developed for this process serving to convert the starting ortho-hydroxybenzhydryl alcohols into the reactive ortho-quinone methides and to control the enantioselectivity of the carbon-carbon bond-forming event via hydrogen-bonding.
authors.affiliation: Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, D-4103 Leipzig, Germany. schneider@chemie.uni-leipzig.de.
authors.forename: Satyajit
authors.initials: S
authors.lastname: Saha
authors.forename: Santosh Kumar
authors.initials: SK
authors.lastname: Alamsetti
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D004583:Electrons; D007211:Indoles / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000473:Alkanes; D007211:Indoles; D009284:Naphthols; D010756:Phosphoric Acids; C030242:phosphoric acid