title: Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.
abstract: Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl-metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.
authors.affiliation: University of York, York, YO24 4PP, UK.
authors.forename: John T R
authors.initials: JT
authors.lastname: Liddon
authors.affiliation: University of York, York, YO24 4PP, UK.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: James
authors.affiliation: University of York, York, YO24 4PP, UK.
authors.forename: Aimee K
authors.initials: AK
authors.lastname: Clarke
authors.affiliation: University of York, York, YO24 4PP, UK.
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.affiliation: University of York, York, YO24 4PP, UK. richard.taylor@york.ac.uk.
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
authors.affiliation: University of York, York, YO24 4PP, UK. william.unsworth@york.ac.uk.
authors.forename: William P
authors.initials: WP
authors.lastname: Unsworth
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002227:Carbazoles; D007211:Indoles; D008698:Mesylates; D011804:Quinolines; D013141:Spiro Compounds; C012077:trifluoromethanesulfonic acid
keywords: carbazoles; catalysis; diversity; quinolines; spirocycles