Gold(I)-Catalyzed Intramolecular Enantioselective Hydroarylation of Allenes with Indoles
- 12 April 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (10) , 1935-1938
- https://doi.org/10.1021/ol070483c
Abstract
Treatment of 2-allenyl indole 4 with a catalytic 1:2 mixture of [(S)-2]Au2Cl2 [(S)-2 = (S)-3,5-tBu-4-MeO-MeOBIPHEP] and AgBF4 in toluene at −10 °C for 17 h led to isolation of tetrahydrocarbazole 5 in 88% yield with 92% ee. The protocol was effective for the cyclization of terminally disubstituted allenes and for the formation of seven-membered rings.Keywords
This publication has 63 references indexed in Scilit:
- Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitationsTetrahedron, 2009
- Intermolecular Hydroamination of Allenes with N-Unsubstituted Carbamates Catalyzed by a Gold(I) N-Heterocyclic Carbene ComplexOrganic Letters, 2008
- Exclusive 5-exo-dig Hydroarylation of o-Alkynyl Biaryls Proceeding via C−H Activation PathwayJournal of the American Chemical Society, 2008
- Gold(I)-Catalyzed Intramolecular Hydroarylation of AllenesThe Journal of Organic Chemistry, 2008
- The Mechanism of the Phosphine-Free Palladium-Catalyzed Hydroarylation of AlkynesJournal of the American Chemical Society, 2006
- Innovative Catalytic Protocols for the Ring‐Closing Friedel–Crafts‐Type Alkylation and Alkenylation of ArenesEuropean Journal of Organic Chemistry, 2006
- Asymmetric Friedel−Crafts Reaction of Indoles with Imines by an Organic CatalystJournal of the American Chemical Society, 2006
- Gold‐Catalyzed Intramolecular Reaction of Indoles with Alkynes: Facile Formation of Eight‐Membered Rings and an Unexpected AllenylationAngewandte Chemie International Edition in English, 2006
- Enantioselective hydrogenation of alkenes and imines by a gold catalystChemical Communications, 2005
- Addition of Olefins to Aromatic Ketones Catalyzed by Rh(I) Olefin ComplexesJournal of the American Chemical Society, 1999