Journal ArticleDOI
Rhodium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides.
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TLDR
Cationic rhodium(I)-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were found to occur in good yields and could be transformed into a variety of products that are difficult or impossible to obtain via directcycloaddition.About:
This article is published in Organic Letters.The article was published on 2005-11-22. It has received 45 citations till now. The article focuses on the topics: Cycloaddition & Intramolecular force.read more
Citations
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Computationally designed and experimentally confirmed diastereoselective rhodium-catalyzed Pauson-Khand reaction at room temperature.
Mu-Hyun Baik,Shivnath Mazumder,Paolo Ricci,James R. Sawyer,Ye-Geun Song,Huijun Wang,P. Andrew Evans +6 more
TL;DR: Experimental studies demonstrate that chloro-enynes provide the optimal σ-electron-withdrawing group to promote polarization and thereby reduce the activation barrier to provide a highly diastereoselective reaction at room temperature.
Journal ArticleDOI
An easy entry to optically active α-amino phosphonic acid derivatives using phase-transfer catalysis (PTC)
Francesco Fini,Gabriele Micheletti,Luca Bernardi,Daniel Pettersen,Mariafrancesca Fochi,Alfredo Ricci +5 more
TL;DR: The unprecedented use of phase-transfer catalysis (PTC) in an asymmetric hydrophosphonylation reaction allows the obtainment of a range of optically active alpha-amino phosphonic acid derivatives directly fromalpha-amido sulfones.
Journal ArticleDOI
DFT Study of the Mechanism and Stereochemistry of the Rh(I)-Catalyzed Diels–Alder Reactions between Electronically Neutral Dienes and Dienophiles
Wei Liao,Zhi-Xiang Yu +1 more
TL;DR: This DFT study of the mechanism and stereochemistry of the Rh-catalyzed Diels-Alder reaction between electronically neutral dienes and dienophiles (alkenes and alkynes), finding that this reaction includes a reaction sequence of oxidative cyclization between diene and alkene/alkyne and a reductive elimination step.
Journal ArticleDOI
Cationic Gold Catalyzes ω-Bromination of Terminal Alkynes and Subsequent Hydroaddition Reactions
Antonio Leyva-Pérez,Paula Rubio-Marqués,Salem S. Al-Deyab,Saud I. Al-Resayes,Avelino Corma,Avelino Corma +5 more
TL;DR: In this paper, the terminal C-H bond is transformed to the corresponding bromoalkyne which is then activated toward nucleophilic attack, which correlates with the structural properties of isolated gold-alkyne complexes.
Journal ArticleDOI
Density Functional Theory Study of the Mechanism of the Rhodium(I)-Catalyzed Conjugated Diene Assisted Allylic C–H Bond Activation and Addition to Alkenes Using Ene-2-dienes As Substrates
Qian Li,Zhi-Xiang Yu +1 more
TL;DR: A DFT study of the mechanism of the conjugated diene assisted, rhodium-catalyzed allylic C–H bond activation and addition to alkenes to synthesize multifunctional tetrahydropyrroles, Tetrahydrofurans, and cyclopentanes from ene-2-diene substrates with good to excellent diastereoselectivities is reported.
References
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Journal ArticleDOI
Transition Metal-Mediated Cycloaddition Reactions
TL;DR: The phytochemical remains of the seven-membered ring formation are still under investigation, but it is clear that the polymethine content of the ring is lower than previously thought, suggesting that it is more likely to be a mixture of 22π and 32σ.
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Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides.
TL;DR: A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4).5H(2)O and 1,10-phenanthroline is described here and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamide.
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Ultrahigh-Quality NOE Spectra
Journal ArticleDOI
Coupling Reactions of Alkynylsilanes Mediated by a Cu(I) Salt: Novel Syntheses of Conjugate Diynes and Disubstituted Ethynes
Yasushi Nishihara,Kazutaka Ikegashira,Kazunori Hirabayashi,Jun Ichi Ando,Atsunori Mori,Tamejiro Hiyama +5 more
TL;DR: The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-Coupling reactions using two different aryl triflates.
Journal ArticleDOI
A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.
Michael O. Frederick,Jason A. Mulder,Michael R. Tracey,Richard P. Hsung,Jian Huang,Kimberly C. M. Kurtz,Lichun Shen,Christopher J. Douglas +7 more
TL;DR: A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides, which should have a significant impact on the future development of synthetic methodologies employing ynamide.
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Paul A. Wender,Thomas E. Jenkins +1 more