36067-19-3Relevant academic research and scientific papers
Visible-light-mediated achmatowicz rearrangement
Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
, p. 30 - 33 (2017/11/28)
Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable 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.
