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Search for "deuterium labeling" in Full Text gives 28 result(s) in Beilstein Journal of Organic Chemistry.
Recent advances in the gold-catalyzed additions to C–C multiple bonds
- He Huang,
- Yu Zhou and
- Hong Liu
Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103
- sp3-hybridized C–H bond can be achieved by undergoing 1,3-addition to a vinyl–carbenoid intermediate [142]. The bicyclo[3.2.1]oct-6-en-2-ones 265 and 267 could be synthesized stereoselectively by this method. Deuterium labeling experiments indicated the cyclization involved an unprecedented 1,3
- via oxidative gold catalysis and provided expedient access to various substituted N- or O-heterocycles (344–351) (Scheme 57). Deuterium labeling experiments were carried out to unveil the reaction mechanism. The results established the anti nature of the alkene functionalization and the indispensable
Graphical Abstract
Scheme 1: Gold-catalyzed addition of alcohols.
Scheme 2: Gold-catalyzed cycloaddition of alcohols.
Scheme 3: Ionic liquids as the solvent in gold-catalyzed cycloaddition.
Scheme 4: Gold-catalyzed cycloaddition of diynes.
Scheme 5: Gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diols.
Scheme 6: Gold-catalyzed cycloaddition of glycols and dihydroxy compounds.
Scheme 7: Gold-catalyzed ring-opening of cyclopropenes.
Scheme 8: Gold-catalyzed intermolecular hydroalkoxylation of alkynes. PR3 = 41–45.
Scheme 9: Gold-catalyzed intramolecular 6-endo-dig cyclization of β-hydroxy-α,α-difluoroynones.
Scheme 10: Gold-catalyzed intermolecular hydroalkoxylation of non-activated olefins.
Scheme 11: Preparation of unsymmetrical ethers from alcohols.
Scheme 12: Expedient synthesis of dihydrofuran-3-ones.
Scheme 13: Catalytic approach to functionalized divinyl ketones.
Scheme 14: Gold-catalyzed glycosylation.
Scheme 15: Gold-catalyzed cycloaddition of aldehydes and ketones.
Scheme 16: Gold-catalyzed annulations of 2-(ynol)aryl aldehydes and o-alkynyl benzaldehydes.
Scheme 17: Gold-catalyzed addition of carboxylates.
Scheme 18: Dual-catalyzed rearrangement reaction of allenoates.
Scheme 19: Meyer–Schuster rearrangement of propargylic alcohols.
Scheme 20: Propargylic alcohol rearrangements.
Scheme 21: Gold-catalyzed synthesis of imines and amine alkylation.
Scheme 22: Hydroamination of allenes and allenamides.
Scheme 23: Gold-catalyzed inter- and intramolecular amination of alkynes and alkenes.
Scheme 24: Gold-catalyzed cycloisomerization of O-propioloyl oximes and β-allenylhydrazones.
Scheme 25: Intra- and intermolecular amination with ureas.
Scheme 26: Gold-catalyzed cyclization of ortho-alkynyl-N-sulfonylanilines and but-3-yn-1-amines.
Scheme 27: Gold-catalyzed piperidine ring synthesis.
Scheme 28: Ring expansion of alkylnyl cyclopropanes.
Scheme 29: Gold-catalyzed annulations of N-propargyl-β-enaminones and azomethine imines.
Scheme 30: Gold(I)-catalyzed cycloisomerization of aziridines.
Scheme 31: AuCl3/AgSbF6-catalyzed intramolecular amination of 2-(tosylamino)phenylprop-1-en-3-ols.
Scheme 32: Gold-catalyzed cyclization via a 7-endo-dig pathway.
Scheme 33: Gold-catalyzed synthesis of fused xanthines.
Scheme 34: Gold-catalyzed synthesis of amides and isoquinolines.
Scheme 35: Gold-catalyzed oxidative cross-coupling reactions of propargylic acetates.
Scheme 36: Gold-catalyzed nucleophilic addition to allenamides.
Scheme 37: Gold-catalyzed direct carbon–carbon bond coupling reactions.
Scheme 38: Gold-catalyzed C−H functionalization of indole/pyrrole heterocycles and non-activated arenes.
Scheme 39: Gold-catalyzed cycloisomerization of cyclic compounds.
Scheme 40: Gold-catalyzed cycloaddition of 1-aryl-1-allen-6-enes and propargyl acetates.
Scheme 41: Gold(I)-catalyzed cycloaddition with ligand-controlled regiochemistry.
Scheme 42: Gold(I)-catalyzed cycloaddition of dienes and enynes.
Scheme 43: Gold-catalyzed intramolecular cycloaddition of 3-alkoxy-1,5-enynes and 2,2-dipropargylmalonates.
Scheme 44: Gold-catalyzed intramolecular cycloaddition of 1,5-allenynes.
Scheme 45: Gold(I)-catalyzed cycloaddition of indoles.
Scheme 46: Gold-catalyzed annulation reactions.
Scheme 47: Gold–carbenoid induced cleavage of a sp3-hybridized C−H bond.
Scheme 48: Furan- and indole-based cascade reactions.
Scheme 49: Tandem process using aromatic alkynes.
Scheme 50: Gold-catalyzed cycloaddition of 1,3-dien-5-ynes.
Scheme 51: Gold-catalyzed cascade cyclization of diynes, propargylic esters, and 1,3-enynyl ketones.
Scheme 52: Tandem reaction of β-phenoxyimino ketones and alkynyl oxime ethers.
Scheme 53: Gold-catalyzed tandem cyclization of enynes, 2-(tosylamino)phenylprop-1-yn-3-ols, and allenoates.
Scheme 54: Cyclization of 2,4-dien-6-yne carboxylic acids.
Scheme 55: Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines.
Scheme 56: Gold-catalyzed tandem reactions of alkynes.
Scheme 57: Aminoarylation and oxyarylation of alkenes.
Scheme 58: Cycloaddition of 2-ethynylnitrobenzene with various alkenes.
Scheme 59: Gold-catalyzed tandem reactions of allenoates and alkynes.
Scheme 60: Gold-catalyzed asymmetric synthesis of 2,3-dihydropyrroles.
Scheme 61: Chiral [NHC–Au(I)]-catalyzed cyclization of enyne.
Scheme 62: Gold-catalyzed hydroaminations and hydroalkoxylations.
Scheme 63: Gold(I)-catalyzed asymmetric hydroalkoxylation of 1,3-dihydroxymethyl-2-alkynylbenzene chromium com...
Scheme 64: Gold-catalyzed synthesis of julolidine derivatives.
Scheme 65: Gold-catalyzed the synthesis of chiral fused heterocycles.
Scheme 66: Gold-catalyzed asymmetric reactions with 3,5-(t-Bu)2-4-MeO-MeOBIPHEP.
Scheme 67: Gold-catalyzed cyclization of o-(alkynyl) styrenes.
Scheme 68: Asymmetric gold(I)-catalyzed redox-neutral domino reactions of enynes.
Scheme 69: Gold(I)-catalyzed enantioselective polyene cyclization reaction.
Scheme 70: Gold(I)-catalyzed enantioselective synthesis of benzopyrans.
Scheme 71: Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.
Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams
- Benito Alcaide and
- Pedro Almendros
Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73
- reveal, 5-exo oxyauration via 16 is restricted by the steric hindrance between the (methoxymethyl)oxy group and the substituents at the quaternary stereocenter. With the aim of trapping the organo–gold intermediate to confirm the mechanism of this reaction, deuterium labeling studies with deuterium oxide
Graphical Abstract
Scheme 1: Gold-catalyzed cyclization of 4-allenyl-2-azetidinones for the preparation of bicyclic β-lactams.
Scheme 2: Possible catalytic cycle for the gold-catalyzed cyclization of 4-allenyl-2-azetidinones.
Scheme 3: Gold- and iron-catalyzed chemodivergent cyclization of ene-allenols for the preparation of oxacycli...
Scheme 4: Gold-catalyzed cyclization of hydroxyallenes for the preparation of five-membered oxacyclic β-lacta...
Figure 1: Free energy profile [kcal mol–1] for the transformation of γ-allenol I into the tetrahydrofuran typ...
Scheme 5: Possible catalytic cycle for the gold-catalyzed cyclization of hydroxyallenes.
Scheme 6: Gold-catalyzed cyclization of MOM-protected α-hydroxyallenes for the preparation of five-membered o...
Scheme 7: Gold-catalyzed cyclization of MOM-protected γ-hydroxyallenes for the preparation of seven-membered ...
Scheme 8: Possible catalytic cycle for the gold-catalyzed cyclization of MOM protected γ-allenol derivatives....
Scheme 9: Au(III)-catalyzed heterocyclization reaction of MOM protected γ-allenol derivative 14a.
Scheme 10: Precious metal-catalyzed formation of benzo-fused pyrrolizinones from N-(2-alkynylphenyl)-β-lactams....
Scheme 11: Gold-catalyzed formation of 5,6-dihydro-8H-indolizin-7-ones from N-(pent-2-en-4-ynyl)-β-lactams.
Scheme 12: Gold-catalyzed formation of non-fused tetrahydrofuryl-β-lactam hemiacetals from 2-azetidinone-tethe...
Scheme 13: Gold-catalyzed formation of spiro tetrahydrofuryl-β-lactam hemiacetals from 2-azetidinone-tethered ...
Scheme 14: Gold-catalyzed formation of fused tetrahydrofuryl-β-lactam hemiacetals from 2-azetidinone-tethered ...
Scheme 15: Possible catalytic cycle for the gold-catalyzed cyclization of MOM protected alkynol derivatives.
Scheme 16: Gold/Brønsted acid co-catalyzed formation of bridged β-lactam acetals from 2-azetidinone-tethered a...
Construction of cyclic enones via gold-catalyzed oxygen transfer reactions
- Leping Liu,
- Bo Xu and
- Gerald B. Hammond
Beilstein J. Org. Chem. 2011, 7, 606–614, doi:10.3762/bjoc.7.71
- cyclization of internal diynes. Proposed solvolysis/cyclization mechanism. Gold-catalyzed cyclization of alkynyl epoxides and the 18O isotopic labeling experiment. Proposed oxygen transfer mechanism. Gold or silver-catalyzed cyclization of alkynyl epoxides and the corresponding deuterium labeling experiment.
Graphical Abstract
Scheme 1: Lewis acid or Brønsted acid-catalyzed alkyne–carbonyl metathesis and a proposed [2 + 2] intermediat...
Scheme 2: Gold-catalyzed cyclization of internal alkynyl ketones.
Scheme 3: Proposed [2 + 2] mechanism for the cyclization of alkynyl ketones.
Scheme 4: Gold-catalyzed cyclization of terminal alkynyl ketones.
Scheme 5: Gold-catalyzed tandem oxygen transfer/Nazarov cyclizations.
Scheme 6: TfOH-mediated cyclization of alkynyl ketones.
Scheme 7: Gold-catalyzed cyclizations of 2-alkynyl-1,5-diketones.
Scheme 8: Designed isotopic labeling experiment for mechanistic studies.
Scheme 9: 18O isotopic experiments.
Scheme 10: B2PLYP/6-311+G(d,p)//B2PLYP/6-31G(d) computed reaction profile, relative energies in kcal/mol.
Scheme 11: Gold-catalyzed cyclization of tethered alkynyl arylaldehydes.
Scheme 12: Gold-catalyzed cyclization of terminal diynes.
Scheme 13: Proposed hydrolysis/cyclization mechanism.
Scheme 14: Gold-catalyzed cyclization of internal diynes.
Scheme 15: Proposed solvolysis/cyclization mechanism.
Scheme 16: Gold-catalyzed cyclization of alkynyl epoxides and the 18O isotopic labeling experiment.
Scheme 17: Proposed oxygen transfer mechanism.
Scheme 18: Gold or silver-catalyzed cyclization of alkynyl epoxides and the corresponding deuterium labeling e...
