related to degree

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

authors

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

publication date

• 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

International Standard Serial Number (ISSN)

• 0002-7863

Digital Object Identifier (DOI)

• 10.1021/ja802491q

PubMed ID

• 18481847

start page

• 7247

end page

• 7249

volume

• 130

issue

• 23