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Article Abstract

This paper reports the kinetic resolution of racemic secondary alcohols (-nucleophiles) via stereoselective intramolecular allylic substitution. The reaction was enabled by synergistic palladium and chiral phosphoric acid catalysis and produced chiral -1,3-disubstituted 1,3-dihydroisobenzofurans with a selective factor of up to 60.9 and a diastereomeric ratio of up to 7.8:1. Asymmetric synthesis of a compound with antihistaminic activity was demonstrated as the application of this methodology.

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http://dx.doi.org/10.1021/acs.joc.3c00236DOI Listing

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