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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Cross-metathesis between alpha-methylene-gamma-butyrolactone and olefins: a dramatic additive effect
Joëlle Moïse1, Stellios Arseniyadis, Janine Cossy
1Laboratoire de Chimie Organique, ESPCI, CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France.
Organic Letters
|April 5, 2007
Summary
This study details olefin cross-metathesis reactions involving gamma-butyrolactones. The process efficiently produces valuable alpha-alkylidene-gamma-butyrolactones with high stereoselectivity using low catalyst amounts.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Gamma-butyrolactones are important structural motifs in organic chemistry.
- Olefin cross-metathesis is a powerful tool for carbon-carbon bond formation.
- Developing efficient methods for functionalizing gamma-butyrolactones is of significant interest.
Purpose of the Study:
- To investigate the olefin cross-metathesis reaction between alpha-methylene-gamma-butyrolactone and terminal olefins.
- To achieve high yields and stereoselectivity in the synthesis of alpha-alkylidene-gamma-butyrolactones.
- To explore the impact of additives on the cross-metathesis efficiency.
Main Methods:
- Employing ruthenium-based catalysts for olefin cross-metathesis.
- Reacting alpha-methylene-gamma-butyrolactone with various terminal olefins.
- Utilizing refluxing dichloromethane (CH2Cl2) as the solvent.
- Investigating the effect of different additives on the reaction outcome.
Main Results:
- Moderate to excellent yields of alpha-alkylidene-gamma-butyrolactones were achieved.
- High E-stereoselectivity was observed in the cross-metathesis products.
- Low catalyst loading was sufficient for efficient transformation.
- Specific additives significantly improved the cross-metathesis process by preventing byproduct formation.
Conclusions:
- Olefin cross-metathesis provides an effective route to alpha-alkylidene-gamma-butyrolactones.
- The reaction is highly stereoselective and proceeds with good yields.
- Additives play a crucial role in optimizing the reaction and suppressing isomerization.
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