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. 2011:7:717-34.
doi: 10.3762/bjoc.7.82. Epub 2011 May 30.

When cyclopropenes meet gold catalysts

Frédéric Miege  1 , Christophe Meyer, Janine Cossy
Affiliations

When cyclopropenes meet gold catalysts

Frédéric Miege et al. Beilstein J Org Chem. 2011.

Abstract

Cyclopropenes as substrates entered the field of gold catalysis in 2008 and have proven to be valuable partners 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.

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Figures

Scheme 1
Scheme 1
General reactivity of cyclopropenes in the presence of gold catalysts.
Scheme 2
Scheme 2
Cationic organogold species generated from cyclopropenone acetals.
Scheme 3
Scheme 3
Rotation barriers around the C2–C3 bond (M06 DFT calculations).
Scheme 4
Scheme 4
Au–C1 bond length in organogold species of type D.
Scheme 5
Scheme 5
Gold-catalyzed addition of alcohols or water to cyclopropene 8.
Scheme 6
Scheme 6
Gold-catalyzed addition of alcohols to cyclopropene 10.
Scheme 7
Scheme 7
Mechanism of the gold-catalyzed addition of alcohols to cyclopropenes.
Scheme 8
Scheme 8
Synthesis of tert-allylic ethers from cyclopropenes and allenes.
Scheme 9
Scheme 9
Oxidation of the intermediate gold–carbene with diphenylsulfoxide.
Scheme 10
Scheme 10
Gold, copper and Lewis acid-catalyzed reactions of cyclopropene 18.
Scheme 11
Scheme 11
Mechanism of the Lewis acid-catalyzed reactions of cyclopropene 18.
Scheme 12
Scheme 12
Gold-catalyzed rearrangement of vinylcyclopropenes 25.
Scheme 13
Scheme 13
Gold-catalyzed rearrangement of cyclopropenes 27 to indenes 28.
Scheme 14
Scheme 14
Gold-catalyzed rearrangement of cyclopropenes 29 to indenes 30.
Scheme 15
Scheme 15
Gold-catalyzed rearrangement of cyclopropenyl ester 34a.
Scheme 16
Scheme 16
Gold-catalyzed reactions of cyclopropenyl esters 34b–34d.
Scheme 17
Scheme 17
Gold-catalyzed reactions of cyclopropenylsilane 34e.
Scheme 18
Scheme 18
Gold-catalyzed rearrangement of cyclopropenylmethyl acetates.
Scheme 19
Scheme 19
Mechanism of the gold-catalyzed rearrangement of cyclopropenes 39.
Scheme 20
Scheme 20
Gold-catalyzed cyclopropanation of styrene with cyclopropene 8.
Scheme 21
Scheme 21
Representative reactions of carbene precursors on gold metal.
Scheme 22
Scheme 22
Intermolecular olefin cyclopropanation with gold carbenes generated from cyclopropenes.
Scheme 23
Scheme 23
Gold-catalyzed formation of trienes from cyclopropenes and furans.
Scheme 24
Scheme 24
Gold-catalyzed formation of trienes from cyclopropenes and furans.
Scheme 25
Scheme 25
Gold-catalyzed formation of trienes from cyclopropenes and furans.
Scheme 26
Scheme 26
Gold-catalyzed cycloisomerization of cyclopropene-ene 59.
Scheme 27
Scheme 27
Gold-catalyzed cycloisomerization of substituted allyl cyclopropenyl carbinyl ethers 62a–62f.
Scheme 28
Scheme 28
Gold-catalyzed cycloisomerization of cyclopropene-enes.
Scheme 29
Scheme 29
Gold-catalyzed cycloisomerization of cyclopropene-ynes.
Scheme 30
Scheme 30
Formation of products arising from a double cleavage process in the gold-catalyzed cycloisomerization of cyclopropene-ynes.
Scheme 31
Scheme 31
Gold-catalyzed cycloisomerization of cyclopropene-ynes involving a double cleavage process.
Scheme 32
Scheme 32
Gold-catalyzed reaction of cyclopropene-ynes, cyclopropene-enes and cyclopropene-allenes.
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References

    1. Hoffmann-Röder A, Krause N. Org Biomol Chem. 2005;3:387–391. doi: 10.1039/b416516k. - DOI - PubMed
    1. Zhang L, Sun J, Kozmin S A. Adv Synth Catal. 2006;348:2271–2296. doi: 10.1002/adsc.200600368. - DOI
    1. Fürstner A, Davies P W. Angew Chem, Int Ed. 2007;46:3410–3449. doi: 10.1002/anie.200604335. - DOI - PubMed
    1. Hashmi A S K. Chem Rev. 2007;107:3180–3211. doi: 10.1021/cr000436x. - DOI - PubMed
    1. Gorin D J, Toste F D. Nature. 2007;446:395–403. doi: 10.1038/nature05592. - DOI - PubMed

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