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Importance of Favorable Non-Covalent Contacts in the Stereoselective Synthesis of Tetrasubstituted Chromanone

Portrait of Laura Andreola, graduate student speaker
Laura Andreola
Graduate Student, Department of Chemistry
University of Georgia
Organic Seminar

Automated transiton state (TS) structure computations for a recently reported Pd-catalysed conjugated addition of arylboronic acids to 2-substituted chromones (Chem Sci, 2020, 11, 4602) reveal unexpected conformations of the key stereodifferentiating benzyl group on the pyridine-dihydroisoquinoline (PyDHIQ) ligand. Detailed analysis shows that stereoselectivity is determined primarily by favorable non-covalent contacts between this benzyl group and the substrates, combined with torsional strain in the primary TS structure leading to the minor stereoisomer. This finding should inform further use and analysis of PyDHIQ and related ligands in other stereoselective transformations.

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