Visible-Light-Mediated Achmatowicz Rearrangement

Org Lett. 2017 Jan 6;19(1):30-33. doi: 10.1021/acs.orglett.6b03237. Epub 2016 Dec 12.

Abstract

Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelf-stable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.

Publication types

  • Research Support, Non-U.S. Gov't