- Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides
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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.
- Schmid, Matthias,Sokol, Kevin R.,Wein, Lukas A.,Torres Venegas, Sofia,Meisenbichler, Christina,Wurst, Klaus,Podewitz, Maren,Magauer, Thomas
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supporting information
p. 6526 - 6531
(2020/09/02)
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- Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes
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A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radical from Togni's reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF3-containing internal alkenylnitriles.
- Zhang, Zi-Qi,Meng, Xiang-Yu,Sheng, Jie,Lan, Quan,Wang, Xi-Sheng
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supporting information
p. 8256 - 8260
(2019/10/16)
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