Directed metal (oxo) aliphatic C-H hydroxylations: Overriding substrate bias

Marinus A. Bigi, Sean A. Reed, M. Christina White

Research output: Contribution to journalArticle

Abstract

The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

Original languageEnglish (US)
Pages (from-to)9721-9726
Number of pages6
JournalJournal of the American Chemical Society
Volume134
Issue number23
DOIs
StatePublished - Jun 13 2012

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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