Synthesis of unstrained Criegee intermediates: inverse α-effect and other protective stereoelectronic forces can stop Baeyer–Villiger rearrangement of γ-hydroperoxy-γ-peroxylactones
Vera A. Vil’, Yana A. Barsegyan, Leah Kuhn, Maria V. Ekimova, Egor A. Semenov, Аlexander А. Korlyukov, Alexander O. Terent’ev, Igor V. Alabugin
Abstract
Protecting stereoelectronic effects prevent Baeyer–Villiger rearrangement and stabilize γ-OX-γ-peroxylactones (X = H, OH), the previously elusive non-strained Criegee intermediates.
Topics & Concepts
ChemistryInverseComputational chemistryMedicinal chemistryStereochemistryPhotochemistryMathematicsGeometryChemical synthesis and alkaloidsMarine Sponges and Natural ProductsSynthetic Organic Chemistry Methods