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Stereospecific Cross-Coupling Reactions With Enantioenriched Electrophiles, Iv Kraja
Stereospecific Cross-Coupling Reactions With Enantioenriched Electrophiles, Iv Kraja
Dissertations, Theses, and Capstone Projects
We have developed a novel palladium-catalyzed stereospecific C(sp3)–C(sp3) Stille cross-coupling reaction between carbastannatrane nucleophiles and α-(trifluoromethyl) benzylic tosylates. This constitutes the first example of a stereospecific C(sp3)–C(sp3) cross-coupling reaction using an enantioenriched electrophile and an alkyltin nucleophile. This system has the potential to be extended to cross-coupling reactions using configurationally stable enantioenriched nucleophiles, thus enabling stereochemical control of two newly formed contiguous stereocenters. Generating enantioenriched α-(trifluoromethyl) benzylic compounds also has importance in pharmaceutical and agrochemical industries.
Through the development of this reaction, our findings show that the addition …