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Planar chiral cyclic ether: asymmetric resolution and chirality transformation
Katsuhiko Tomooka1, Nobuyuki Komine, Daisuke Fujiki
1Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan. ktomooka@apc.titech.ac.jp
Stable planar chirality was discovered in a nine-membered cyclic ether. This novel chiral building block was synthesized using kinetic resolution, yielding an enantiomerically enriched compound.
Area of Science:
- Organic Chemistry
- Stereochemistry
Background:
- Planar chirality is a type of chirality where chirality arises from the arrangement of substituents around a plane.
- Cyclic ethers are versatile compounds with applications in various chemical syntheses.
Purpose of the Study:
- To investigate the synthesis and properties of a novel nine-membered diallylic cyclic ether.
- To explore the potential of this compound as a chiral building block.
Main Methods:
- Kinetic resolution of a racemic mixture of the cyclic ether.
- Characterization of the enantiomerically enriched product.
Main Results:
- Remarkably stable planar chirality was observed in the nine-membered diallylic cyclic ether.
- Enantiomerically enriched ether was successfully prepared via kinetic resolution.
Conclusions:
- The synthesized nine-membered diallylic cyclic ether exhibits stable planar chirality.
- This compound represents a valuable new chiral building block for organic synthesis.
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