American Chemical Society
jo3c00417_si_001.pdf (23.14 MB)

Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules

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journal contribution
posted on 2023-06-16, 04:18 authored by Lenin Kumar Verdhi, Asit Ghosh, Natalia Fridman, Alex M. Szpilman
A copper and chiral nitroxide co-catalyzed aerobic enantioselective oxidation process has been developed that allows access to axially chiral molecules. Two complementary atroposelective approaches, oxidative kinetic resolution (OKR) and desymmetrization, were studied using ambient air as the stoichiometric terminal oxidant. OKR of rac-N-arylpyrrole alcohols and rac-biaryl alcohols affords the optically pure compounds with er up to 3.5:96.5 and 5.5:94.5, respectively. Desymmetrization of prochiral diols provides axially chiral biaryl compounds with er up to 99:1.