Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters

[Image: see text] A new chemoenzymatic one-pot strategy has been developed for the synthesis of α-hydroxy half-esters containing consecutive quaternary and tertiary stereocenters using asymmetric cascade catalysis. In this study, an asymmetric Ca(2+)-catalyzed [2,3]-Wittig rearrangement reaction was...

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Autores principales: Murre, Aleksandra, Erkman, Kristin, Järving, Ivar, Kanger, Tõnis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359131/
https://www.ncbi.nlm.nih.gov/pubmed/34396014
http://dx.doi.org/10.1021/acsomega.1c02973
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author Murre, Aleksandra
Erkman, Kristin
Järving, Ivar
Kanger, Tõnis
author_facet Murre, Aleksandra
Erkman, Kristin
Järving, Ivar
Kanger, Tõnis
author_sort Murre, Aleksandra
collection PubMed
description [Image: see text] A new chemoenzymatic one-pot strategy has been developed for the synthesis of α-hydroxy half-esters containing consecutive quaternary and tertiary stereocenters using asymmetric cascade catalysis. In this study, an asymmetric Ca(2+)-catalyzed [2,3]-Wittig rearrangement reaction was proven to be suitable for a combination with porcine liver esterase-mediated hydrolysis resulting in the enhanced enantiomeric purity of the obtained products in a one-pot synthesis compared to the stepwise method.
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spelling pubmed-83591312021-08-13 Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters Murre, Aleksandra Erkman, Kristin Järving, Ivar Kanger, Tõnis ACS Omega [Image: see text] A new chemoenzymatic one-pot strategy has been developed for the synthesis of α-hydroxy half-esters containing consecutive quaternary and tertiary stereocenters using asymmetric cascade catalysis. In this study, an asymmetric Ca(2+)-catalyzed [2,3]-Wittig rearrangement reaction was proven to be suitable for a combination with porcine liver esterase-mediated hydrolysis resulting in the enhanced enantiomeric purity of the obtained products in a one-pot synthesis compared to the stepwise method. American Chemical Society 2021-07-28 /pmc/articles/PMC8359131/ /pubmed/34396014 http://dx.doi.org/10.1021/acsomega.1c02973 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 Murre, Aleksandra
Erkman, Kristin
Järving, Ivar
Kanger, Tõnis
Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title_full Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title_fullStr Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title_full_unstemmed Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title_short Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
title_sort asymmetric chemoenzymatic one-pot synthesis of α-hydroxy half-esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359131/
https://www.ncbi.nlm.nih.gov/pubmed/34396014
http://dx.doi.org/10.1021/acsomega.1c02973
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