Gold-Catalyzed Rearrangement of (Silylcyclopropenyl)methyl Ethers into (Silylmethylene)cyclopropanes

Florence Hiault; Alexis Archambeau; Frédéric Miege; Christophe Meyer; Janine Cossy

doi:10.1055/s-0035-1561486

Synthesis, Table of Contents

Synthesis 2016; 48(19): 3165-3174
DOI: 10.1055/s-0035-1561486

paper

Gold-Catalyzed Rearrangement of (Silylcyclopropenyl)methyl Ethers into (Silylmethylene)cyclopropanes

Florence Hiault

Laboratory of Organic Chemistry, Institute of Chemistry, Biology and Innovation (CBI) ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: christophe.meyer@espci.fr Email: janine.cossy@espci.fr

,

Alexis Archambeau

Laboratory of Organic Chemistry, Institute of Chemistry, Biology and Innovation (CBI) ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: christophe.meyer@espci.fr Email: janine.cossy@espci.fr

,

Frédéric Miege

Laboratory of Organic Chemistry, Institute of Chemistry, Biology and Innovation (CBI) ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: christophe.meyer@espci.fr Email: janine.cossy@espci.fr

,

Christophe Meyer*

Laboratory of Organic Chemistry, Institute of Chemistry, Biology and Innovation (CBI) ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: christophe.meyer@espci.fr Email: janine.cossy@espci.fr

,

Janine Cossy*

Laboratory of Organic Chemistry, Institute of Chemistry, Biology and Innovation (CBI) ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: christophe.meyer@espci.fr Email: janine.cossy@espci.fr

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Abstract

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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.

Key words

cyclopropenes - gold catalysis - strained cycles - rearrangement - hydride transfer

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References

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Supplementary Material

Supporting Information