A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction
The Journal of Organic Chemistry2008Vol. 73(13), pp. 5064–5068
Citations Over TimeTop 10% of 2008 papers
Abstract
Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.
Related Papers
- → Allenes and Transition Metals: A Diverging Approach to Heterocycles(2004)92 cited
- → An efficient cyclopentenone formation via an allene oxide(1988)56 cited
- → Synthesis of the stemodane carbon skeleton: nonstereoselective photoaddition of allene to a cyclopentenone and a novel rearrangement reaction(1982)17 cited
- → Organic Syntheses by Means of Noble Metal Compounds. XXXVII. Carbonylation of Allene-Palladium Chloride Complexes(1968)13 cited
- → Palladium(II)‐Mediated Cyclization—Carbonylation of 4‐Yn‐1‐ones: Facile Access to 2‐Cyclopentenone Carboxylates.(2002)