1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.
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.
Chen
Ke
K
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Richter
Jeremy M
JM
Baran
Phil S
PS
D000438:Alcohols / Q000138:chemical synthesis*; D002219:Carbamates / Q000737:chemistry*; D003500:Cyclization; D006868:Hydrolysis; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry
D000438:Alcohols; D002219:Carbamates; D020005:Propanols; C006463:allyl alcohol