This article reports diastereoselective cyclization with chiral sulfinamides as nucleophiles in two reaction pathways:(1) intramolecular allylic substitution and (2) sequential aerobic oxidation with aza-Michael addition. These reactions were enabled by synergistic palladium and Brønsted acid catalysis and produced chiral isoindolines with good yields of 55−92% and high diastereoselectivities of 10:1 to >20:1 dr.
This paper reports the kinetic resolution of racemic
secondary
alcohols (O-nucleophiles) via stereoselective intramolecular
allylic substitution. The reaction was enabled by synergistic palladium
and chiral phosphoric acid catalysis and produced chiral cis-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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