Synthetic utility of epoxides for chiral functionalization of isoxazoles

Jared K. Nelson, Christopher T. Burns, Miles P. Smith, Brendan Twamley, N. R. Natale

Research output: Contribution to journalArticlepeer-review

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).

Original languageEnglish
Pages (from-to)3078-3082
Number of pages5
JournalTetrahedron Letters
Volume49
Issue number19
DOIs
StatePublished - May 5 2008

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