Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6526-6531Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02296
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Funding
- European Research Council under the European Union's Horizon 2020 Research and Innovation Programme [714049]
- Center for Molecular Biosciences (CMBI)
- German Academic Scholarship Foundation
- German National Academy of Sciences Leopoldina
- Tyrolean Science Fund (TWF) [F.16642/5-2019, UNI-0404/2354]
- Austrian Science Fund (FWF) [M-2005]
- European Research Council (ERC) [714049] Funding Source: European Research Council (ERC)
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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.
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