Literature DB >> 22734508

Z-selective metathesis homocoupling of 1,3-dienes by molybdenum and tungsten monoaryloxide pyrrolide (MAP) complexes.

Erik M Townsend1, Richard R Schrock, Amir H Hoveyda.   

Abstract

Molybdenum or tungsten monoaryloxide pyrrolide (MAP) complexes that contain OHIPT as the aryloxide (hexaisopropylterphenoxide) are effective catalysts for homocoupling of simple (E)-1,3-dienes to give (E,Z,E)-trienes in high yield and with high Z selectivities. A vinylalkylidene MAP species was shown to have the expected syn structure in an X-ray study. MAP catalysts that contain OHMT (hexamethylterphenoxide) are relatively inefficient.

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Year:  2012        PMID: 22734508      PMCID: PMC3417118          DOI: 10.1021/ja303220j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  23 in total

1.  Macrolide Analogues of the Novel Immunosuppressant Sanglifehrin: New Application of the Ring-Closing Metathesis Reaction.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

2.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

3.  Z-Selective and Syndioselective Ring-Opening Metathesis Polymerization (ROMP) Initiated by MonoAryloxidePyrrolide (MAP) Catalysts.

Authors:  Margaret M Flook; Laura C H Gerber; Galia T Debelouchina; Richard R Schrock
Journal:  Macromolecules       Date:  2010-09-28       Impact factor: 5.985

4.  Stereoselective cyclopolymerization of 1,6-heptadiynes: access to alternating cis-trans-1,2-(cyclopent-1-enylene)vinylenes by fine-tuning of molybdenum imidoalkylidenes.

Authors:  Udo Anders; Oskar Nuyken; Michael R Buchmeiser; Klaus Wurst
Journal:  Angew Chem Int Ed Engl       Date:  2002-11-04       Impact factor: 15.336

5.  Isolation of pure disubstituted E olefins through Mo-catalyzed Z-selective ethenolysis of stereoisomeric mixtures.

Authors:  Smaranda C Marinescu; Daniel S Levine; Yu Zhao; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-07-07       Impact factor: 15.419

6.  Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors:  Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

7.  Highly concise routes to epothilones: the total synthesis and evaluation of epothilone 490.

Authors:  Kaustav Biswas; Hong Lin; Jon T Njardarson; Mark D Chappell; Ting-Chao Chou; Yongbiao Guan; William P Tong; Lifeng He; Susan B Horwitz; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

8.  Fundamental studies of tungsten alkylidene imido monoalkoxidepyrrolide complexes.

Authors:  Annie J Jiang; Jeffrey H Simpson; Peter Müller; Richard R Schrock
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

9.  Highly Z-selective metathesis homocoupling of terminal olefins.

Authors:  Annie J Jiang; Yu Zhao; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

10.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962

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  9 in total

1.  Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors:  Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

2.  Concise syntheses of insect pheromones using Z-selective cross metathesis.

Authors:  Myles B Herbert; Vanessa M Marx; Richard L Pederson; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-10       Impact factor: 15.336

3.  Alkene chemoselectivity in ruthenium-catalyzed Z-selective olefin metathesis.

Authors:  Jeffrey S Cannon; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

4.  Synthesis of Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds through stereoselective catalytic cross-metathesis.

Authors:  Elizabeth T Kiesewetter; Robert V O'Brien; Elsie C Yu; Simon J Meek; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2013-04-15       Impact factor: 15.419

5.  Investigations into Ruthenium Metathesis Catalysts with Six-Membered Chelating NHC Ligands: Relationship between Catalyst Structure and Stereoselectivity.

Authors:  Koji Endo; Myles B Herbert; Robert H Grubbs
Journal:  Organometallics       Date:  2013-09-23       Impact factor: 3.876

6.  Synthesis of Tungsten Imido Alkylidene Complexes that Contain an Electron-Withdrawing Imido Ligand.

Authors:  Jonathan C Axtell; Richard R Schrock; Peter Müller; Stacey J Smith; Amir H Hoveyda
Journal:  Organometallics       Date:  2014-09-17       Impact factor: 3.876

7.  Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands.

Authors:  Erik M Townsend; Jakub Hyvl; William P Forrest; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal:  Organometallics       Date:  2014-09-22       Impact factor: 3.876

8.  Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.

Authors:  Katharina Herz; Maren Podewitz; Laura Stöhr; Dongren Wang; Wolfgang Frey; Klaus R Liedl; Suman Sen; Michael R Buchmeiser
Journal:  J Am Chem Soc       Date:  2019-05-09       Impact factor: 15.419

9.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

  9 in total

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