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Search for "gold-stabilized allylic cations" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

When cyclopropenes meet gold catalysts

Frédéric Miege,
Christophe Meyer and
Janine Cossy

Beilstein J. Org. Chem. 2011, 7, 717–734, doi:10.3762/bjoc.7.82

in a variety of gold-catalyzed reactions. The different contributions in this growing research area are summarized in this review. Keywords: cyclopropenes; gold carbenes; gold catalysis; gold-stabilized allylic cations; ring-opening; Review Introduction Homogeneous gold catalysis has become a

, little information is available on the modulation and tuning of the reactivity by the choice of the gold ligand. Nucleophilic addition to gold-stabilized allylic cations generated from cyclopropenes Intermolecular addition of oxygen nucleophiles In 2008, Lee et al. reported several gold-catalyzed

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Graphical Abstract

Scheme 1: General reactivity of cyclopropenes in the presence of gold catalysts.

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Scheme 2: Cationic organogold species generated from cyclopropenone acetals.

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Scheme 3: Rotation barriers around the C2–C3 bond (M06 DFT calculations).

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Scheme 4: Au–C1 bond length in organogold species of type D.

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Scheme 5: Gold-catalyzed addition of alcohols or water to cyclopropene 8.

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Scheme 6: Gold-catalyzed addition of alcohols to cyclopropene 10.

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Scheme 7: Mechanism of the gold-catalyzed addition of alcohols to cyclopropenes.

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Scheme 8: Synthesis of tert-allylic ethers from cyclopropenes and allenes.

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Scheme 9: Oxidation of the intermediate gold–carbene with diphenylsulfoxide.

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Scheme 10: Gold, copper and Lewis acid-catalyzed reactions of cyclopropene 18.

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Scheme 11: Mechanism of the Lewis acid-catalyzed reactions of cyclopropene 18.

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Scheme 12: Gold-catalyzed rearrangement of vinylcyclopropenes 25.

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Scheme 13: Gold-catalyzed rearrangement of cyclopropenes 27 to indenes 28.

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Scheme 14: Gold-catalyzed rearrangement of cyclopropenes 29 to indenes 30.

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Scheme 15: Gold-catalyzed rearrangement of cyclopropenyl ester 34a.

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Scheme 16: Gold-catalyzed reactions of cyclopropenyl esters 34b–34d.

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Scheme 17: Gold-catalyzed reactions of cyclopropenylsilane 34e.

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Scheme 18: Gold-catalyzed rearrangement of cyclopropenylmethyl acetates.

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Scheme 19: Mechanism of the gold-catalyzed rearrangement of cyclopropenes 39.

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Scheme 20: Gold-catalyzed cyclopropanation of styrene with cyclopropene 8.

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Scheme 21: Representative reactions of carbene precursors on gold metal.

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Scheme 22: Intermolecular olefin cyclopropanation with gold carbenes generated from cyclopropenes.

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Scheme 23: Gold-catalyzed formation of trienes from cyclopropenes and furans.

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Scheme 24: Gold-catalyzed formation of trienes from cyclopropenes and furans.

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Scheme 25: Gold-catalyzed formation of trienes from cyclopropenes and furans.

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Scheme 26: Gold-catalyzed cycloisomerization of cyclopropene-ene 59.

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Scheme 27: Gold-catalyzed cycloisomerization of substituted allyl cyclopropenyl carbinyl ethers 62a–62f.

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Scheme 28: Gold-catalyzed cycloisomerization of cyclopropene-enes.

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Scheme 29: Gold-catalyzed cycloisomerization of cyclopropene-ynes.

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Scheme 30: Formation of products arising from a double cleavage process in the gold-catalyzed cycloisomerizati...

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Scheme 31: Gold-catalyzed cycloisomerization of cyclopropene-ynes involving a double cleavage process.

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Scheme 32: Gold-catalyzed reaction of cyclopropene-ynes, cyclopropene-enes and cyclopropene-allenes.

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Review

Published 30 May 2011

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