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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
Efficient allyl to propenyl isomerization in functionally diverse compounds with a thermally modified Grubbs
Stephen Hanessian1, Simon Giroux, Andreas Larsson
1Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
Organic Letters
|November 17, 2006
Summary
This study introduces a new method for synthesizing 2-propenyl derivatives using Grubbs catalyst. The reaction efficiently converts allylic compounds into valuable intermediates without unwanted side reactions.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Allylic compounds are versatile building blocks in organic synthesis.
- Developing efficient and selective methods for functionalizing allylic groups is crucial.
- Existing methods may suffer from limited substrate scope or undesired side reactions.
Purpose of the Study:
- To develop a novel catalytic method for the synthesis of 2-propenyl derivatives.
- To investigate the scope and limitations of the developed reaction.
- To provide a straightforward route to functionalized olefins.
Main Methods:
- Heating allylic compounds in methanol with Grubbs second-generation catalyst.
- Utilizing a substrate concentration of 0.075 M.
- Employing 10 mol % of the catalyst.
Main Results:
- The reaction successfully yielded corresponding 2-propenyl derivatives from ketones, esters, and lactams.
- No further conjugation was observed in the products.
- The method demonstrated applicability to various terminal olefins, including O- and N-allyl ethers.
Conclusions:
- The developed method offers an efficient and selective route to 2-propenyl derivatives.
- Grubbs catalyst facilitates the transformation of C-allylic appendages under mild conditions.
- This methodology expands the synthetic toolkit for accessing functionalized olefins.
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