Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis
Alonso J. Argüelles
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorSiyuan Sun
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorBrenna G. Budaitis
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Pavel Nagorny
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorAlonso J. Argüelles
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorSiyuan Sun
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorBrenna G. Budaitis
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Pavel Nagorny
Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 USA
Search for more papers by this authorAbstract
We present an expedient and economical route to a new spiroketal-based C2-symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in iridium-catalyzed hydroarylations (up to 95 % ee), palladium-catalyzed allylic alkylations (up to 97 % ee), intermolecular palladium-catalyzed Heck couplings (up to 94 % ee), and rhodium-catalyzed dehydroalanine hydrogenation (up to 93 % ee).
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