The -Wittig rearrangement of (E)-crotyl propargylic ethers, when induced with a t-BuLi /chiral bis(oxazoline) complex, is shown to provide high enantioselectivity (up to 89% ee) along with high diastereoselectivity.
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Asymmetric [2,3]-Wittig Rearrangement Induced by a Chiral Carbanion Whose Chirality Was Transferred from an Epoxide
โ Scribed by Sasaki, Michiko; Higashi, Mariko; Masu, Hyuma; Yamaguchi, Kentaro; Takeda, Kei
- Book ID
- 127317847
- Publisher
- American Chemical Society
- Year
- 2005
- Tongue
- English
- Weight
- 57 KB
- Volume
- 7
- Category
- Article
- ISSN
- 1523-7060
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Enantioselective [2,3]-Wittig Rearrangement Induced by Asymmetric Lithiation with a t-Butyllithium / Chiral Bis(oxazoline) System. -The use of a chiral bis(oxazoline) is effective as ligand for the enantioselective [2,3]-Wittig rearrangement of (E)-and (Z)-propargyl ethers. -(TOMOOKA,