Synthetic Utility of Epoxides for Chiral Functionalization of Isoxazoles
Jared K Nelson1, Christopher T Burns, Miles P Smith
1Department of Chemistry, University of Idaho, Moscow, ID 83844-2343.
Abstract:
The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b).
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