80351-93-5Relevant academic research and scientific papers
New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions
Massa, Antonio,Siniscalchi, Francesca R.,Bugatti, Valeria,Lattanzi, Alessandra,Scettri, Arrigo
, p. 1277 - 1283 (2002)
Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)-furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used as oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)4/L-DET or Ti(O-i-Pr)4/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomerically enriched Ti(IV)/BINOL/H2O complexes.
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.
