Bisguanidinium-catalyzed formation of oxygen-containing quaternary stereogenic carbon centers†
Abstract
We report bisguanidinium-catalyzed enantioconvergent halogenophilic substitution reactions (SN2X) that lead to the formation of C(sp3)–O bonds using racemic tertiary bromides with hydroxylamides or phenols as nucleophiles. These approaches gave direct access to a series of oxygen-containing quaternary stereogenic carbon centers, which are common moieties in bioactive compounds. We also demonstrated the utility of these methodologies through concise syntheses of enantiopure bicalutamide and chiral fibrates.
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