Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules

[Image: see text] 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...

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Autores principales: Verdhi, Lenin Kumar, Ghosh, Asit, Fridman, Natalia, Szpilman, Alex M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10337035/
https://www.ncbi.nlm.nih.gov/pubmed/37322607
http://dx.doi.org/10.1021/acs.joc.3c00417
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author Verdhi, Lenin Kumar
Ghosh, Asit
Fridman, Natalia
Szpilman, Alex M.
author_facet Verdhi, Lenin Kumar
Ghosh, Asit
Fridman, Natalia
Szpilman, Alex M.
author_sort Verdhi, Lenin Kumar
collection PubMed
description [Image: see text] 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.
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spelling pubmed-103370352023-07-13 Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules Verdhi, Lenin Kumar Ghosh, Asit Fridman, Natalia Szpilman, Alex M. J Org Chem [Image: see text] 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. American Chemical Society 2023-06-16 /pmc/articles/PMC10337035/ /pubmed/37322607 http://dx.doi.org/10.1021/acs.joc.3c00417 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Verdhi, Lenin Kumar
Ghosh, Asit
Fridman, Natalia
Szpilman, Alex M.
Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title_full Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title_fullStr Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title_full_unstemmed Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title_short Catalytic Atroposelective Aerobic Oxidation Approaches to Axially Chiral Molecules
title_sort catalytic atroposelective aerobic oxidation approaches to axially chiral molecules
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10337035/
https://www.ncbi.nlm.nih.gov/pubmed/37322607
http://dx.doi.org/10.1021/acs.joc.3c00417
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