One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation

[Image: see text] An enantio- and diastereoselective Cu–H-catalyzed silylation of acyclic secondary alcohols with a vicinal quaternary stereocenter is reported. The reaction kinetically selects one out of four stereoisomers, affording the fastest-reacting stereoisomer as the silyl ether in enantio-...

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Autores principales: Papadopulu, Zaneta, Kazeroonian, Novid, Irran, Elisabeth, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9954319/
https://www.ncbi.nlm.nih.gov/pubmed/36855454
http://dx.doi.org/10.1021/acsorginorgau.1c00050
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author Papadopulu, Zaneta
Kazeroonian, Novid
Irran, Elisabeth
Oestreich, Martin
author_facet Papadopulu, Zaneta
Kazeroonian, Novid
Irran, Elisabeth
Oestreich, Martin
author_sort Papadopulu, Zaneta
collection PubMed
description [Image: see text] An enantio- and diastereoselective Cu–H-catalyzed silylation of acyclic secondary alcohols with a vicinal quaternary stereocenter is reported. The reaction kinetically selects one out of four stereoisomers, affording the fastest-reacting stereoisomer as the silyl ether in enantio- and diastereomerically enriched form. The obtained motif with a quaternary carbon atom in the β-position of the hydroxy group is otherwise not easy to access.
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spelling pubmed-99543192023-02-27 One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation Papadopulu, Zaneta Kazeroonian, Novid Irran, Elisabeth Oestreich, Martin ACS Org Inorg Au [Image: see text] An enantio- and diastereoselective Cu–H-catalyzed silylation of acyclic secondary alcohols with a vicinal quaternary stereocenter is reported. The reaction kinetically selects one out of four stereoisomers, affording the fastest-reacting stereoisomer as the silyl ether in enantio- and diastereomerically enriched form. The obtained motif with a quaternary carbon atom in the β-position of the hydroxy group is otherwise not easy to access. American Chemical Society 2021-12-09 /pmc/articles/PMC9954319/ /pubmed/36855454 http://dx.doi.org/10.1021/acsorginorgau.1c00050 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Papadopulu, Zaneta
Kazeroonian, Novid
Irran, Elisabeth
Oestreich, Martin
One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title_full One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title_fullStr One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title_full_unstemmed One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title_short One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu–H-Catalyzed Enantioselective Silylation
title_sort one out of four: kinetic resolution of stereoisomeric mixtures of secondary alcohols with a quaternary carbon atom in the β-position by cu–h-catalyzed enantioselective silylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9954319/
https://www.ncbi.nlm.nih.gov/pubmed/36855454
http://dx.doi.org/10.1021/acsorginorgau.1c00050
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