A Highly Regioselective Ring-Opening Metathesis−Cross Metathesis Process Modulated by the Electronic Effects of the Cross Metathesis Partner: An Entry to Quaternary Prolines

2009 ◽  
Vol 74 (4) ◽  
pp. 1736-1739 ◽  
Author(s):  
Javier Carreras ◽  
Alberto Avenoza ◽  
Jesús H. Busto ◽  
Jesús M. Peregrina
Keyword(s):  
Ring Opening ◽  
Electronic Effects ◽  
Cross Metathesis ◽  
The Cross

scholarly journals Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

2015 ◽  
Vol 11 ◽  
pp. 1876-1880 ◽  
Author(s):  
Meriem K Abderrezak ◽  
Kristýna Šichová ◽  
Nancy Dominguez-Boblett ◽  
Antoine Dupé ◽  
Zahia Kabouche ◽  
...  
Keyword(s):  
Methyl Acrylate ◽  
Ring Opening ◽  
Building Blocks ◽  
Epoxide Ring ◽  
Cross Metathesis ◽  
Saturated Compound ◽  
Polyfunctional Compounds ◽  
The Cross ◽  
High Yields ◽  
Nucleophilic Ring Opening

The cross metathesis of 1,2-epoxy-5-hexene (1) with methyl acrylate and acrylonitrile was investigated as an entry to the synthesis of polyfunctional compounds. The resulting cross metathesis products were hydrogenated in a tandem fashion employing the residual ruthenium from the metathesis step as the hydrogenation catalyst. Interestingly, the epoxide ring remained unreactive toward this hydrogenation method. The saturated compound resulting from the cross metathesis of 1 with methyl acrylate was transformed by means of nucleophilic ring-opening of the epoxide to furnish a diol, an alkoxy alcohol and an amino alcohol in high yields.

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

2018 ◽  
Author(s):  
Nicholas Marshall
Keyword(s):  
Thin Films ◽  
Contact Angle ◽  
Cyclic Voltammetry ◽  
Polymer Films ◽  
Conjugated Polymer ◽  
Ring Opening ◽  
Molecular Wires ◽  
Metathesis Polymerization ◽  
Cross Metathesis ◽  
Active Ester

A set of experiments in surface-initiated ring-opening metathesis polymerization, including end-functionalization of growing brushes and contact angle/cyclic voltammetry measurements. We report preparation and CV of two different conjugated polymer films, and several endgroup and sidechain functionalization experiments using cross-metathesis and active ester substitution.<br>

Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

2015 ◽  
Vol 68 (12) ◽  
pp. 1815 ◽  
Author(s):  
Steven-Alan G. Abel ◽  
Wesley J. Olivier ◽  
Richard L. Pederson ◽  
Alex C. Bissember ◽  
Jason A. Smith
Keyword(s):  
The Self ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
The Cross

(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Synlett ◽  
2021 ◽  
Author(s):  
Loránd Kiss ◽  
Zsanett Benke ◽  
Melinda Nonn ◽  
Attila M. Remete ◽  
Santos Fustero
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Nitrile Oxide ◽  
Amino Acid Derivatives ◽  
Selective Synthesis ◽  
Chemical Transformations ◽  
Bond Functionalization ◽  
Cross Metathesis ◽  
Chlorosulfonyl Isocyanate ◽  
Biological Potential

AbstractThis Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis.1 Introduction2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis8 Summary and Outlook9 List of Abbreviations

Low Catalyst Loading in the Cross Metathesis of Olefins with Methyl Vinyl Ketone

Synlett ◽  
2013 ◽  
Vol 24 (10) ◽  
pp. 1193-1196 ◽  
Author(s):  
Christian Slugovc ◽  
Muddasar Abbas ◽  
Anita Leitgeb
Keyword(s):  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Catalyst Loading ◽  
Methyl Vinyl ◽  
Cross Metathesis ◽  
The Cross ◽  
Low Catalyst Loading

scholarly journals Computational study of productive and non-productive cycles in fluoroalkene metathesis

2015 ◽  
Vol 11 ◽  
pp. 2150-2157 ◽  
Author(s):  
Markéta Rybáčková ◽  
Jan Hošek ◽  
Ondřej Šimůnek ◽  
Viola Kolaříková ◽  
Jaroslav Kvíčala
Keyword(s):  
Computational Study ◽  
Catalytic Cycle ◽  
Dft Study ◽  
Cross Metathesis ◽  
High Preference ◽  
The Cross

A detailed DFT study of the mechanism of metathesis of fluoroethene, 1-fluoroethene, 1,1-difluoroethene, cis- and trans-1,2-difluoroethene, tetrafluoroethene and chlorotrifluoroethene catalysed with the Hoveyda–Grubbs 2nd generation catalyst was performed. It revealed that a successful metathesis of hydrofluoroethenes is hampered by a high preference for a non-productive catalytic cycle proceeding through a ruthenacyclobutane intermediate bearing fluorines in positions 2 and 4. Moreover, the calculations showed that the cross-metathesis of perfluoro- or perhaloalkenes should be a feasible process and that the metathesis is not very sensitive to stereochemical issues.

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