Synthesis of Benzonorcaradienes by Gold(I)-Catalyzed [4+3] Annulation
- 25 October 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (45), 14480-14481
- https://doi.org/10.1021/ja066694e
Abstract
A formal [4 + 3]-annulation of vinyl arenes and diynyl propargyl esters is described. A mechanism involving cationic phosphinegold(I)-catalyzed tandem cyclopropanation/hydroarylation to produce the benzonorcaradiene products is proposed. In accord with this mechanism, the alkynyl cyclopropane can also be prepared with excellent regio- and diastereocontrol.Keywords
This publication has 8 references indexed in Scilit:
- Mechanisms of the Transition Metal-Mediated Hydroarylation of Alkynes and AllenesOrganometallics, 2006
- Gold(I)-Catalyzed Stereoselective Olefin CyclopropanationJournal of the American Chemical Society, 2005
- Gold catalysis: five new bonds by a domino hydroarylation/cycloisomerizationTetrahedron, 2005
- Intramolecular Hydroarylation of Alkynes Catalyzed by Platinum or Gold: Mechanism and endo SelectivityChemistry – A European Journal, 2005
- Ruthenium-Catalyzed Cyclopropanation of Alkenes Using Propargylic Carboxylates as Precursors of VinylcarbenoidsThe Journal of Organic Chemistry, 2003
- A new ruthenium-catalyzed cyclopropanation of alkenes using propargylic acetates as a precursor of vinylcarbenoidsTetrahedron Letters, 2003
- Domino Reactions in Organic SynthesisChemical Reviews, 1996
- Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(2-naphthyl)butan-2-one. Direct Chemical Evidence for the Formation of the Norcaradiene System in the Intramolecular Buchner ReactionThe Journal of Organic Chemistry, 1995