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General synthetic approach to functionalized dihydrooxepines
K C Nicolaou1, Ruocheng Yu, Lei Shi
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States. kcn@scripps.edu
A new three-step method creates functionalized 4,5-dihydrooxepines from cyclohexenones. This process utilizes a regioselective Baeyer-Villiger oxidation and enol phosphate intermediates for efficient synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Cyclohexenones are versatile starting materials in organic synthesis.
- Accessing functionalized oxepine rings remains a synthetic challenge.
Purpose of the Study:
- To develop an efficient synthetic route to functionalized 4,5-dihydrooxepines.
- To explore the utility of Baeyer-Villiger oxidation and enol phosphate intermediates in this transformation.
Main Methods:
- A three-step reaction sequence starting from cyclohexenones.
- Regioselective Baeyer-Villiger oxidation of cyclohexenones.
- Functionalization of the resulting lactone via an enol phosphate intermediate.
Main Results:
- Successful synthesis of functionalized 4,5-dihydrooxepines.
- Demonstration of regioselectivity in the Baeyer-Villiger oxidation step.
- Establishment of a versatile route applicable to various cyclohexenone substrates.
Conclusions:
- A novel and efficient three-step sequence for synthesizing functionalized 4,5-dihydrooxepines has been established.
- The developed method offers a valuable tool for accessing substituted oxepine derivatives.
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