title: Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles.
abstract: A high-yielding, divergent approach to generate either spirocyclic indolenines or carbazoles from a common indole-tethered propargyl alcohol precursor is described, with mechanistic insight provided. Either product can be obtained upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford (±)-actinopolymorphol B is also reported.
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Michael J
authors: MJ
authors: James
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Rosa E
authors: RE
authors: Clubley
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Kleopas Y
authors: KY
authors: Palate
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Thomas J
authors: TJ
authors: Procter
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Anthony C
authors: AC
authors: Wyton
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Peter
authors: P
authors: O'Brien
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: Richard J K
authors: RJ
authors: Taylor
authors: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors: William P
authors: WP
authors: Unsworth
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D012835:Silver Nitrate / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001688:Biological Products; D002227:Carbazoles; D026121:Indole Alkaloids; D020005:Propanols; C000603524:actinopolymorphol B; D012835:Silver Nitrate; C028255:propargyl alcohol