A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs Dedicated to Professor Paul Wender for his pioneering and inspirational work on complexity generating organometallic reactions for streamlining complex molecule synthesis

Dustin J. Covell, M. Christina White

Research output: Contribution to journalArticlepeer-review

Abstract

Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C-H activation/ resolution is evaluated against the state-of-the-art. The C-H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility.

Original languageEnglish (US)
Pages (from-to)7771-7778
Number of pages8
JournalTetrahedron
Volume69
Issue number36
DOIs
StatePublished - Sep 9 2013

Keywords

  • Allylic alcohols
  • Allylic oxidation
  • C-H oxidation
  • Enantioselective
  • Palladium
  • Sulfoxide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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