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Updated: Aug 6, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ruthenium-catalyzed alkylative lactonization and carbocyclization
Barry M Trost1, Andrew McClory
1Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
A novel ruthenium complex catalyzes the efficient synthesis of valuable lactones from allene carboxylic acids and olefins. This mild reaction tolerates diverse functional groups, enabling broader synthetic applications.
Area of Science:
- Organometallic Chemistry
- Organic Synthesis
- Catalysis
Background:
- Lactones are important heterocyclic compounds with wide applications in pharmaceuticals and materials science.
- Developing efficient and selective methods for lactone synthesis remains a key challenge in organic chemistry.
Purpose of the Study:
- To develop a novel catalytic system for the synthesis of five- and six-membered lactones.
- To explore the scope and limitations of the new reaction using various substrates.
Main Methods:
- Utilizing a cationic ruthenium complex, [CpRu(NCCH3)3]PF6, as a catalyst.
- Investigating the coupling reaction between monosubstituted allene carboxylic acids and alpha,beta-unsaturated olefins.
Main Results:
- The ruthenium catalyst effectively promoted the coupling reaction under mild conditions.
- The reaction successfully yielded various five- and six-membered lactones.
- The presence of diverse functional groups on the starting materials was tolerated.
Conclusions:
- The developed ruthenium-catalyzed reaction provides a facile route to substituted lactones.
- The mild conditions and functional group tolerance make this method attractive for complex molecule synthesis.
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