Intramolecular Pauson−Khand Reactions of α,β-Unsaturated Esters and Related Electron-Deficient Olefins
- 5 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (7) , 2975-2978
- https://doi.org/10.1021/jo026828g
Abstract
The intramolecular Pauson−Khand (PK) reaction of a variety of electron-poor enynes having an ester, cyano, or phosphonate group at the olefin terminus is described. Depending on the reaction conditions and substitution at the enyne, their dicobalthexacarbonyl complexes led preferentially to the exocyclic 1,3-diene or to the PK cyclopentenone product. In general, the 1,3-diene was obtained as the major product under N-oxide-promoted conditions, while the PK product was selectively formed in refluxing acetonitrile.Keywords
This publication has 7 references indexed in Scilit:
- endo-Selective Intramolecular Pauson-Khand Reactions ofγ-Oxygenated-α,β-unsaturated PhenylsulfonesChemistry – A European Journal, 2001
- Synthesis of Tricyclic Aromatic Compounds by the Intramolecular Pauson−Khand Reaction Promoted by Molecular Sieves,1The Journal of Organic Chemistry, 2000
- Pauson-Khand reaction of activated olefinsTetrahedron Letters, 1999
- Dienes from the thermolysis of dicobalthexacarbonyl-complexed enynes: Mechanistic insightTetrahedron Letters, 1998
- The sequence of a stepwise AdE reaction and intramolecular Pauson-Khand cycloaddition as an entry into the synthesis of polycyclic compoundsJournal of the American Chemical Society, 1992
- An unusual case of Khand-Pauson cyclization involving the participation of a conjugated double bond. A promising sequence for the assemblage of polycyclic frameworkTetrahedron Letters, 1991
- Synthesis of conjugated dienes using cobalt acetylene complexesJournal of the Chemical Society, Chemical Communications, 1974