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DOI: 10.1055/s-0035-1561486
Gold-Catalyzed Rearrangement of (Silylcyclopropenyl)methyl Ethers into (Silylmethylene)cyclopropanes
Publication History
Received: 13 May 2016
Accepted after revision: 08 June 2016
Publication Date:
27 July 2016 (online)
Dedicated to the memory of Professor Jean-François Normant, a remarkable mentor and scientific personality.
Abstract
Methoxymethyl ethers derived from 2-(dimethylphenylsilyl)cycloprop-1-enyl carbinols undergo gold-catalyzed rearrangement leading to [(Z)-(dimethylphenylsilyl)methylene]cyclopropanes in moderate to high yields with methyl formate as a byproduct. This transformation proceeds by initial regioselective ring opening of the three-membered ring leading to an α-silyl vinyl gold carbenoid. This latter organogold species evolves by 1,5-hydride transfer, which triggers subsequent rearrangement involving loss of methyl formate, 2π-electrocyclization of the resulting allylic cation, and elimination of the metal to regenerate the catalyst.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561486.
- Supporting Information