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Literature DB >> 21718001

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

Smaranda C Marinescu¹, Daniel S Levine, Yu Zhao, Richard R Schrock, Amir H Hoveyda.

Abstract

Monoaryloxide-pyrrolide (MAP) complexes of molybdenum were employed for the selective ethenolysis of 1,2-disubstituted Z olefins in the presence of the corresponding E olefins. Reactions were performed in the presence of 0.02-3.0 mol % catalyst at 22 °C under 20 atm ethylene. We have demonstrated that the Z isomer of an easily accessible E:Z mixture can be destroyed through ethenolysis and the E alkene thereby isolated readily in high yield and exceptional stereoisomeric purity.

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Year: 2011 PMID： 21718001 PMCID： PMC3145000 DOI： 10.1021/ja205002v

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

18 in total

1. Highly selective ruthenium metathesis catalysts for ethenolysis.

Authors: Renee M Thomas; Benjamin K Keitz; Timothy M Champagne; Robert H Grubbs
Journal: J Am Chem Soc Date: 2011-04-21 Impact factor: 15.419

2. 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

3. Understanding d(0)-olefin metathesis catalysts: which metal, which ligands?

Authors: Albert Poater; Xavier Solans-Monfort; Eric Clot; Christophe Copéret; Odile Eisenstein
Journal: J Am Chem Soc Date: 2007-06-09 Impact factor: 15.419

4. Chelated ruthenium catalysts for Z-selective olefin metathesis.

Authors: Koji Endo; Robert H Grubbs
Journal: J Am Chem Soc Date: 2011-05-12 Impact factor: 15.419

5. Z-selective homodimerization of terminal olefins with a ruthenium metathesis catalyst.

Authors: Benjamin K Keitz; Koji Endo; Myles B Herbert; Robert H Grubbs
Journal: J Am Chem Soc Date: 2011-06-08 Impact factor: 15.419

6. Ethenolysis reactions catalyzed by imido alkylidene monoaryloxide monopyrrolide (MAP) complexes of molybdenum.

Authors: Smaranda C Marinescu; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-08-12 Impact factor: 15.419

7. 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

8. Highly Z- and enantioselective ring-opening/cross-metathesis reactions catalyzed by stereogenic-at-Mo adamantylimido complexes.

Authors: Ismail Ibrahem; Miao Yu; Richard R Schrock; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-03-25 Impact factor: 15.419

9. Z-selective olefin metathesis processes catalyzed by a molybdenum hexaisopropylterphenoxide monopyrrolide complex.

Authors: Margaret M Flook; Annie J Jiang; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-06-17 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

17 in total

1. 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

10. Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.

Authors: Vanessa M Marx; Myles B Herbert; Benjamin K Keitz; Robert H Grubbs
Journal: J Am Chem Soc Date: 2012-12-21 Impact factor: 15.419

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

1. Highly selective ruthenium metathesis catalysts for ethenolysis.

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

3. Understanding d(0)-olefin metathesis catalysts: which metal, which ligands?

4. Chelated ruthenium catalysts for Z-selective olefin metathesis.

5. Z-selective homodimerization of terminal olefins with a ruthenium metathesis catalyst.

6. Ethenolysis reactions catalyzed by imido alkylidene monoaryloxide monopyrrolide (MAP) complexes of molybdenum.

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

8. Highly Z- and enantioselective ring-opening/cross-metathesis reactions catalyzed by stereogenic-at-Mo adamantylimido complexes.

9. Z-selective olefin metathesis processes catalyzed by a molybdenum hexaisopropylterphenoxide monopyrrolide complex.

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

1. 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.

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

3. Partial synthesis of ganglioside and lysoganglioside lipoforms as internal standards for MS quantification.

4. Ru-Based Z-Selective Metathesis Catalysts with Modified Cyclometalated Carbene Ligands.

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

Review 6. Recent advances in ruthenium-based olefin metathesis.

7. Z-Selective olefin metathesis reactions promoted by tungsten oxo alkylidene complexes.

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

9. Z-Selective ethenolysis with a ruthenium metathesis catalyst: experiment and theory.

10. Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.