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1,3-diol synthesis via controlled, radical-mediated C-H functionalization

Academic Article
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Overview

related to degree

  • Richter, Jeremy, Ph.D. in Chemistry, Scripps Research 2003 - 2008

authors

  • Chen, K.
  • Richter, Jeremy
  • Baran, Phil

publication date

  • June 2008

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radical-mediated C-H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann-Löffler-Freytag reaction, cyclization, and hydrolysis to provide the 1,3-diols. In addition to the 10 examples presented herein, the syntheses of four natural products are facilitated by this directed oxyfunctionalization. This methodology is demonstrated to be orthogonal to other known C-H oxidations. Finally, this sequence is efficient, practical, inexpensive, and scalable.

subject areas

  • Alcohols
  • Carbamates
  • Cyclization
  • Hydrolysis
  • Oxidation-Reduction
  • Propanols
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja802491q

PubMed ID

  • 18481847
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Additional Document Info

start page

  • 7247

end page

  • 7249

volume

  • 130

issue

  • 23

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