Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones

[Image: see text] Two synthetic protocols for the conversion of 1-phenylphosphinan-4-ones to novel P-stereogenic 1-phenylphosphin-2-en-4-ones by enantioselective deprotonation followed by oxidation and by asymmetric organocatalytic halogenation accompanied by elimination have been developed. These t...

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Autores principales: Łastawiecka, Elżbieta, Frynas, Sławomir, Pietrusiewicz, K. Michał
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279496/
https://www.ncbi.nlm.nih.gov/pubmed/33900770
http://dx.doi.org/10.1021/acs.joc.0c03055
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author Łastawiecka, Elżbieta
Frynas, Sławomir
Pietrusiewicz, K. Michał
author_facet Łastawiecka, Elżbieta
Frynas, Sławomir
Pietrusiewicz, K. Michał
author_sort Łastawiecka, Elżbieta
collection PubMed
description [Image: see text] Two synthetic protocols for the conversion of 1-phenylphosphinan-4-ones to novel P-stereogenic 1-phenylphosphin-2-en-4-ones by enantioselective deprotonation followed by oxidation and by asymmetric organocatalytic halogenation accompanied by elimination have been developed. These two-step one-pot transformations provide convenient access to optically active 1-phenylphosphin-2-en-4-one 1-sulfide and 1-phenylphosphin-2-en-4-one 1-oxide of 96 and 55% enantiomeric purities, respectively.
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spelling pubmed-82794962021-07-15 Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones Łastawiecka, Elżbieta Frynas, Sławomir Pietrusiewicz, K. Michał J Org Chem [Image: see text] Two synthetic protocols for the conversion of 1-phenylphosphinan-4-ones to novel P-stereogenic 1-phenylphosphin-2-en-4-ones by enantioselective deprotonation followed by oxidation and by asymmetric organocatalytic halogenation accompanied by elimination have been developed. These two-step one-pot transformations provide convenient access to optically active 1-phenylphosphin-2-en-4-one 1-sulfide and 1-phenylphosphin-2-en-4-one 1-oxide of 96 and 55% enantiomeric purities, respectively. American Chemical Society 2021-04-26 2021-05-07 /pmc/articles/PMC8279496/ /pubmed/33900770 http://dx.doi.org/10.1021/acs.joc.0c03055 Text en © 2021 The Authors. Published by American Chemical Society 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 Łastawiecka, Elżbieta
Frynas, Sławomir
Pietrusiewicz, K. Michał
Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title_full Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title_fullStr Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title_full_unstemmed Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title_short Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
title_sort desymmetrization approach to the synthesis of optically active p-stereogenic phosphin-2-en-4-ones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279496/
https://www.ncbi.nlm.nih.gov/pubmed/33900770
http://dx.doi.org/10.1021/acs.joc.0c03055
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AT pietrusiewiczkmichał desymmetrizationapproachtothesynthesisofopticallyactivepstereogenicphosphin2en4ones

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