Mechanistic Insights into the Gold-Catalyzed Cycloisomerization of Bromoallenyl Ketones: Ligand-Controlled Regioselectivity
- 8 May 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (22), 6940-6941
- https://doi.org/10.1021/ja802144t
Abstract
Through computational and experimental studies, the mechanisms of gold-catalyzed cycloisomerization of bromoallenyl ketones in toluene have been elucidated. The divergent 1,2-migrations for the Au(I)- and Au(III)-catalyzed reactions have been investigated, and the results confirmed that the regiochemistry is ligand-dependent in cases of Au(PR3)L (L = Cl, OTf, BF4, and SbF6) catalysts.Keywords
This publication has 39 references indexed in Scilit:
- Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized HeterocyclesJournal of the American Chemical Society, 2008
- The Reaction Mechanism of the Hydroamination of Alkenes Catalyzed by Gold(I)−Phosphine: The Role of the Counterion and the N-Nucleophile Substituents in the Proton-Transfer StepJournal of the American Chemical Society, 2008
- AuCl-Catalyzed Synthesis of Benzyl-Protected Substituted Phenols: A Formal [3+3] ApproachOrganic Letters, 2007
- Gold(I)-Catalyzed [2 + 2]-Cycloaddition of AllenenesJournal of the American Chemical Society, 2007
- Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted FuransAngewandte Chemie-International Edition, 2007
- A Highly Efficient Preparative Method of α-Ylidene-β-Diketones via AuIII-Catalyzed Acyl Migration of Propargylic EstersJournal 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, 2006
- Efficient Synthesis of Cyclopentenones from Enynyl Acetates via Tandem Au(I)-Catalyzed 3,3-Rearrangement and the Nazarov ReactionJournal of the American Chemical Society, 2006
- Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters: Expeditious Access to Highly Functionalized 2,3-Indoline-Fused CyclobutanesJournal of the American Chemical Society, 2005
- Intramolecular Hydroarylation of Alkynes Catalyzed by Platinum or Gold: Mechanism and endo SelectivityChemistry – A European Journal, 2005