39489-42-4Relevant articles and documents
Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides
Schmid, Matthias,Sokol, Kevin R.,Wein, Lukas A.,Torres Venegas, Sofia,Meisenbichler, Christina,Wurst, Klaus,Podewitz, Maren,Magauer, Thomas
supporting information, p. 6526 - 6531 (2020/09/02)
We report our studies on the development of a catalytic cycloisomerization of 2,2-disubstituted neopentylic epoxides to produce highly substituted tetralins and chromanes. Termination of the sequence occurs via Friedel-Crafts-type alkylation of the remote (hetero)arene linker. The transformation is efficiently promoted by sulfuric acid and proceeds best in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as the solvent. Variation of the substitution pattern provided detailed insights into the migration tendencies and revealed a competing disproportionation pathway of dihydronaphthalenes.