Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides | Zendy

Matthias Schmid | Zendy; Kevin Rafael Sokol | Zendy; Lukas A. Wein | Zendy; Sofia Torres Venegas | Zendy; Christina Meisenbichler | Zendy; Klaus Wurst | Zendy; Maren Podewitz | Zendy; Thomas Magauer | Zendy

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Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides

Author(s) -

Matthias Schmid,

Kevin Rafael Sokol,

Lukas A. Wein,

Sofia Torres Venegas,

Christina Meisenbichler,

Klaus Wurst,

Maren Podewitz,

Thomas Magauer

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02296

Subject(s) - cycloisomerization , chemistry , disproportionation , vicinal , alkylation , catalysis , sulfuric acid , linker , solvent , combinatorial chemistry , organic chemistry , stereochemistry , computer science , operating system

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.

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