Preparation of chiral isoxazole carbinols via catalytic asymmetric Corey-Bakshi-Shibata reduction

Kevin C. Rider, David J. Burkhart, Chun Li, Andrew R. Mckenzie, Jared K. Nelson, Nicholas R. Natale

Research output: Contribution to journalArticlepeer-review

Abstract

A diverse set of isoxazoles, with activity in three different disease categories, was reduced asymmetrically from pro-chiral ketones to chiral alcohols using the Corey-Bakshi-Shibata methodology at the α, β, and γ positions relative to the C-5-methyl of the isoxazole. The experiments described provide an easy route to hydroxylated isoxazoles that represent the common CYP-450 3A4 metabolic site.

Original languageEnglish
Pages (from-to)97-107
Number of pages11
JournalArkivoc
Volume2010
Issue number8
DOIs
StatePublished - 2010

Keywords

  • Asymmetric synthesis
  • Catalysis
  • Isoxazole
  • Oxazaborolidine
  • Reduction

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