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Communication

1,3-Diol Synthesis via Controlled, Radical-Mediated C−H Functionalization

Supporting Info

Ke Chen, Jeremy M. Richter and Phil S. Baran

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037

J. Am. Chem. Soc., 2008, 130 (23), pp 7247–7249

DOI: 10.1021/ja802491q

Publication Date (Web): May 16, 2008

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−Lffler−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.

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