Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights
- 25 January 2013
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 19 (10), 3415-3425
- https://doi.org/10.1002/chem.201204087
Abstract
A detailed study of the Ni-catalyzed [4+3+2] cycloaddition reaction between ethyl cyclopropylideneacetate and dienynes has been conducted, resulting in the development of a new method for the synthesis of compounds containing nine-membered rings. We studied the reactivity of various dienynes, together with their substituent and conformational effects. The mechanism of the reaction was probed by examining the stoichiometric reactions of the Ni complexes and dienynes.Funding Information
- Society of Synthetic Organic Chemistry of Japan
This publication has 98 references indexed in Scilit:
- Transition‐Metal‐Catalyzed Cycloadditions for the Synthesis of Eight‐Membered CarbocyclesChemistry – An Asian Journal, 2010
- Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene RearrangementThe Journal of Organic Chemistry, 2009
- A short history of SHELXActa Crystallographica Section A Foundations of Crystallography, 2007
- Efficient Catalytic Insertion of Acetylenes into a Carbon−Carbon Single Bond of Nonstrained Cyclic Compounds under Mild ConditionsJournal of the American Chemical Society, 2006
- Diverse Methods for Medium Ring SynthesisAccounts of Chemical Research, 1998
- Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halidesThe Journal of Organic Chemistry, 1992
- Intramolecular cycloaddition reactions of dienyne ethers. Synthesis of bridgehead dienes and their thermal rearrangementsThe Journal of Organic Chemistry, 1988
- Metallacycloalkane, VI. Fünf‐ bis siebengliedrige (2,2′‐Bipyridin)nickelacycloalkane aus Methylencyclopropan und Nickel(0)‐VerbindungenEuropean Journal of Inorganic Chemistry, 1983
- Preparation and reactions of phosphine nickelocyclopentanesJournal of the American Chemical Society, 1978
- Configurations in Unsymmetrically N,N-Disubstituted AmidesJournal of the American Chemical Society, 1963