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Asymmetric [2,3]-Wittig rearrangements with chiral, phosphorus anion-stabilizing groups

✍ Scribed by Scott E. Denmark; Paula C. Miller


Book ID
103428430
Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
375 KB
Volume
36
Category
Article
ISSN
0040-4039

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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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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,