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Copper-Catalyzed Remote Asymmetric Three-Component Sulfonylation Using SO2 as the Sulfur Source to Access Chiral
Jiale Li1, Wenli Yan1, Shuning Liu2
1Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
A novel copper-catalyzed reaction efficiently synthesizes chiral allylic sulfones from simple precursors. This method offers high enantioselectivity and broad functional group tolerance under mild conditions.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- Sulfonylation reactions are crucial for synthesizing organosulfur compounds.
- Developing enantioselective methods for allylic sulfone synthesis remains a challenge.
Purpose of the Study:
- To report a novel copper-catalyzed three-component reaction for enantioselective sulfonylation.
- To synthesize chiral allylic sulfones from yne-allylic esters, sulfur dioxide, and cyclopropan-1-ols.
Main Methods:
- Copper-catalyzed three-component reaction.
- Utilized yne-allylic esters, sulfur dioxide, and cyclopropan-1-ols as starting materials.
- Investigated the reaction mechanism involving copper-allenylidene intermediates and ε-addition of γ-keto sulfinate.
Main Results:
- Achieved efficient synthesis of chiral allylic sulfones.
- Obtained high enantioselectivity, up to 96% ee.
- Demonstrated broad functional group compatibility and good yields under mild conditions.
Conclusions:
- The developed protocol provides an efficient route to valuable chiral allylic sulfones.
- The reaction proceeds through a unique mechanism involving copper-allenylidene intermediates.
- This method offers a practical approach for asymmetric sulfonylation in organic synthesis.
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