α-Photooxygenation of chiral aldehydes with singlet oxygen

Organocatalytic α-oxygenation of chiral aldehydes with photochemically generated singlet oxygen allows synthesizing chiral 3-substituted 1,2-diols. Stereochemical results indicate that the reaction in the presence of diarylprolinol silyl ethers is highly diastereoselective and that the configuration...

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Autores principales: Walaszek, Dominika J, Jawiczuk, Magdalena, Durka, Jakub, Drapała, Olga, Gryko, Dorota
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6720656/
https://www.ncbi.nlm.nih.gov/pubmed/31501676
http://dx.doi.org/10.3762/bjoc.15.205
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author Walaszek, Dominika J
Jawiczuk, Magdalena
Durka, Jakub
Drapała, Olga
Gryko, Dorota
author_facet Walaszek, Dominika J
Jawiczuk, Magdalena
Durka, Jakub
Drapała, Olga
Gryko, Dorota
author_sort Walaszek, Dominika J
collection PubMed
description Organocatalytic α-oxygenation of chiral aldehydes with photochemically generated singlet oxygen allows synthesizing chiral 3-substituted 1,2-diols. Stereochemical results indicate that the reaction in the presence of diarylprolinol silyl ethers is highly diastereoselective and that the configuration of a newly created stereocenter at the α-position depends predominantly on the catalyst structure. The absolute configuration of chiral 1,2-diols has been unambiguously established based on electronic circular dichroism (ECD) and TD-DFT methods.
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spelling pubmed-67206562019-09-09 α-Photooxygenation of chiral aldehydes with singlet oxygen Walaszek, Dominika J Jawiczuk, Magdalena Durka, Jakub Drapała, Olga Gryko, Dorota Beilstein J Org Chem Full Research Paper Organocatalytic α-oxygenation of chiral aldehydes with photochemically generated singlet oxygen allows synthesizing chiral 3-substituted 1,2-diols. Stereochemical results indicate that the reaction in the presence of diarylprolinol silyl ethers is highly diastereoselective and that the configuration of a newly created stereocenter at the α-position depends predominantly on the catalyst structure. The absolute configuration of chiral 1,2-diols has been unambiguously established based on electronic circular dichroism (ECD) and TD-DFT methods. Beilstein-Institut 2019-08-30 /pmc/articles/PMC6720656/ /pubmed/31501676 http://dx.doi.org/10.3762/bjoc.15.205 Text en Copyright © 2019, Walaszek et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Walaszek, Dominika J
Jawiczuk, Magdalena
Durka, Jakub
Drapała, Olga
Gryko, Dorota
α-Photooxygenation of chiral aldehydes with singlet oxygen
title α-Photooxygenation of chiral aldehydes with singlet oxygen
title_full α-Photooxygenation of chiral aldehydes with singlet oxygen
title_fullStr α-Photooxygenation of chiral aldehydes with singlet oxygen
title_full_unstemmed α-Photooxygenation of chiral aldehydes with singlet oxygen
title_short α-Photooxygenation of chiral aldehydes with singlet oxygen
title_sort α-photooxygenation of chiral aldehydes with singlet oxygen
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6720656/
https://www.ncbi.nlm.nih.gov/pubmed/31501676
http://dx.doi.org/10.3762/bjoc.15.205
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