title: Synthetic Utility of Epoxides for Chiral Functionalization of Isoxazoles.
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).
authors.affiliation: Department of Chemistry, University of Idaho, Moscow, ID 83844-2343.
authors.forename: Jared K
authors.initials: JK
authors.lastname: Nelson
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Burns
authors.forename: Miles P
authors.initials: MP
authors.lastname: Smith
authors.forename: Brendan
authors.initials: B
authors.lastname: Twamley
authors.forename: N R
authors.initials: NR
authors.lastname: Natale