14294-62-3Relevant academic research and scientific papers
Unique reactivity of anti - and syn-acetoxypyranones en route to oxidopyrylium intermediates leading to a cascade process
Woodall, Erica L.,Simanis, Justin A.,Hamaker, Christopher G.,Goodell, John R.,Mitchell, T. Andrew
, p. 3270 - 3273 (2013)
Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.
Visible-light-mediated achmatowicz rearrangement
Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
supporting information, 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.
