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Enantioselective

Tomooka¹, Yamamoto, Nakai

¹Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552 (Japan).

Angewandte Chemie (International Ed. in English)

|January 29, 2000

Summary

This study introduces the first enantioselective [1,2] Wittig rearrangement, converting benzyl ethers to alcohols with high enantioselectivity using a chiral bis(dihydrooxazole) ligand.

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Area of Science:

Organic Chemistry
Asymmetric Synthesis

Background:

The [1,2] Wittig rearrangement is a valuable carbon-carbon bond-forming reaction.
Achieving enantioselectivity in this rearrangement has been a significant challenge.

Purpose of the Study:

To develop the first catalytic enantioselective [1,2] Wittig rearrangement.
To utilize a chiral bis(dihydrooxazole) ligand for asymmetric induction.

Main Methods:

Catalytic rearrangement of benzyl ethers.
Employing a chiral bis(dihydrooxazole) as an external ligand.
Analysis of enantioselectivity using chiral chromatography.

Main Results:

The rearrangement of benzyl ethers to alcohols proceeded with high enantioselectivity (>60% ee).
A catalytic amount of the chiral ligand was sufficient for high asymmetric induction.
This represents the first successful enantioselective [1,2] Wittig rearrangement.

Conclusions:

Catalytic enantioselective [1,2] Wittig rearrangement is now achievable.
Chiral bis(dihydrooxazole) ligands are effective for asymmetric synthesis in this reaction class.

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