Thioureas as Ligands in the Pd-Catalyzed Intramolecular Pauson−Khand Reaction

Tang, Yefeng; Deng, Lujiang; Zhang, Yangdong; Dong, Guangbin; Chen, Jiahua; Yang, Zhen

doi:10.1021/ol050410y

Cited by 93 publications

(46 citation statements)

References 29 publications

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“…Optical rotation measurements were conducted on a Perkin–Elmer 241 polarimeter at 589 nm. Enynes 5 [71], 2a [72], 2b – e [46], 1a [73], 1b [74], 1c , d [75], 1e [73], and 6 [64] were prepared according to published procedures. 1 H, 13 C NMR and mass spectrometry data for compounds 3a , b [23], 3c , d [75], 3e [76] and 4a – e [46] were described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Pradal¹,

Chao²,

Toullec³

et al. 2011

Beilstein J. Org. Chem.

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SummaryA comprehensive study on the asymmetric gold-catalyzed cycloisomerization reaction of heteroatom tethered 1,6-enynes is described. The cycloisomerization reactions were conducted in the presence of the chiral cationic Au(I) catalyst consisting of (R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP-(AuCl)2 complex and silver salts (AgOTf or AgNTf2) in toluene under mild conditions to afford functionalized bicyclo[4.1.0]heptene derivatives. The reaction conditions were found to be highly substrate-dependent, the best results being obtained in the case of oxygen-tethered enynes. The formation of bicyclic derivatives, including cyclopropyl pentasubstituted ones, was reported in moderate to good yields and in enantiomeric excesses up to 99%.

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Section: Methodsmentioning

confidence: 99%

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Pradal¹,

Chao²,

Toullec³

et al. 2011

Beilstein J. Org. Chem.

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“…A catalyst system of dicobalt octacarbonyl-tetramethylthiourea and carbon monoxide was reported [992] and used in synthesis toward micrandilactone [993]. Palladium catalyzed Pauson-Khand reactions using tetramethylthiourea and carbon monoxide [994]. Molybdenum mediated Pauson-Khand reactions at room temperature [995].…”

Section: Carbonylations Of Alkynes (Including the Pauson-khand Reaction)mentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…During this transformation, TMTU was used for the first time to promote the efficiency in CÀH transformation as an additive, although thiourea has been broadly used as a ligand in different transformations. [10] The yield decreased dramatically in the absence of TMTU, which may arise from the stabilizing ability of TMTU to Pd II species (cf. entries 5 and 13).…”

mentioning

confidence: 99%

Direct Imidation to Construct 1H‐Benzo[d]imidazole through Pd^II‐Catalyzed CH Activation Promoted by Thiourea

Xiao

Wang

Liu

et al. 2009

Chemistry A European J

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140

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Die beispiellose Struktur des marinen Naturstoffs Brevetoxin B wurde 1981 von den Arbeitsgruppen um Nakanishi und Clardy aufgeklärt. Das leiterförmige Molekülgerüst dieses kondensierten Polyethers, die starke Toxizität und der faszinierende Wirkmechanismus durch Angriff am spannungsgesteuerten Natriumkanal sorgten für Aufmerksamkeit. Syntheseversuche führten zur Entwicklung zahlreicher neuer Methoden und Strategien zum Aufbau von Etherringen und wurden schließlich durch die Totalsynthesen von Brevetoxin B und einigen verwandten, ähnlich anspruchsvollen Zielverbindungen gekrönt. Unter den marinen Polyethern nimmt Maitotoxin als kompliziertester und giftigster Vertreter eine Sonderstellung ein; die Verbindung ist der größte bekannte nichtpolymere Naturstoff überhaupt. Dieser Aufsatz beginnt mit einer kurzen Geschichte zur Isolierung der Biotoxine und beleuchtet ihre biologischen Eigenschaften und Wirkmechanismen. Dann werden Syntheseversuche beschrieben, wobei besonders neue Methoden berücksichtigt werden, die im Laufe dieser Studien entwickelt wurden. Den Abschluss bilden eine Diskussion der noch nicht abgeschlossenen Totalsynthese von Maitotoxin sowie ein Ausblick auf die weitere Entwicklung des Forschungsgebiets.

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Thioureas as Ligands in the Pd-Catalyzed Intramolecular Pauson−Khand Reaction

Abstract: [reaction: see text] The thiourea-Pd complex was established as a novel type of catalyst in the PKR of allylpropargylamine, and the demonstrated chemistry may prove to be valuable for developing thiuorea as a ligand for the Pd-catalyzed Pauson-Khand reaction.

Cited by 93 publications

References 29 publications

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Transition metals in organic synthesis: Highlights for the year 2005

Direct Imidation to Construct 1H‐Benzo[d]imidazole through Pd^II‐Catalyzed CH Activation Promoted by Thiourea

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Thioureas as Ligands in the Pd-Catalyzed Intramolecular Pauson−Khand Reaction

Abstract: [reaction: see text] The thiourea-Pd complex was established as a novel type of catalyst in the PKR of allylpropargylamine, and the demonstrated chemistry may prove to be valuable for developing thiuorea as a ligand for the Pd-catalyzed Pauson-Khand reaction.

Cited by 93 publications

References 29 publications

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

Transition metals in organic synthesis: Highlights for the year 2005

Direct Imidation to Construct 1H‐Benzo[d]imidazole through PdII‐Catalyzed CH Activation Promoted by Thiourea

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Product

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About

Direct Imidation to Construct 1H‐Benzo[d]imidazole through Pd^II‐Catalyzed CH Activation Promoted by Thiourea