A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis
| Autor: | Keary M. Engle, Lucas J. Oxtoby, Van T. Tran, Yang Gao, Mingyu Liu, Zhonglin Liu, Zi-Qi Li |
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| Rok vydání: | 2021 |
| Předmět: |
Fluorocarbons
Molecular Structure Group strategy Enantioselective synthesis Stereoisomerism General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Article Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound Colloid and Surface Chemistry chemistry Hexafluorophosphate Organofluorine compounds Selectivity Palladium Vicinal |
| Zdroj: | J Am Chem Soc |
| Popis: | The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds. |
| Databáze: | OpenAIRE |
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