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