Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling

[Image: see text] Herein, we report the development of a catalytic enantioselective addition of N-substituted allyl equivalents to ketone electrophiles through use of Cu-catalyzed reductive coupling to access important chiral 1,2-aminoalcohol synthons in high levels of regio-, diastereo-, and enanti...

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Autores principales: Klake, Raphael K., Edwards, Mytia D., Sieber, Joshua D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8384047/
https://www.ncbi.nlm.nih.gov/pubmed/34347500
http://dx.doi.org/10.1021/acs.orglett.1c02258
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author Klake, Raphael K.
Edwards, Mytia D.
Sieber, Joshua D.
author_facet Klake, Raphael K.
Edwards, Mytia D.
Sieber, Joshua D.
author_sort Klake, Raphael K.
collection PubMed
description [Image: see text] Herein, we report the development of a catalytic enantioselective addition of N-substituted allyl equivalents to ketone electrophiles through use of Cu-catalyzed reductive coupling to access important chiral 1,2-aminoalcohol synthons in high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed including the identification of a reversible ketone allylation step that has not been previously reported in Cu-catalyzed reductive coupling.
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spelling pubmed-83840472022-08-04 Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling Klake, Raphael K. Edwards, Mytia D. Sieber, Joshua D. Org Lett [Image: see text] Herein, we report the development of a catalytic enantioselective addition of N-substituted allyl equivalents to ketone electrophiles through use of Cu-catalyzed reductive coupling to access important chiral 1,2-aminoalcohol synthons in high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed including the identification of a reversible ketone allylation step that has not been previously reported in Cu-catalyzed reductive coupling. American Chemical Society 2021-08-04 2021-08-20 /pmc/articles/PMC8384047/ /pubmed/34347500 http://dx.doi.org/10.1021/acs.orglett.1c02258 Text en © 2021 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 Klake, Raphael K.
Edwards, Mytia D.
Sieber, Joshua D.
Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title_full Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title_fullStr Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title_full_unstemmed Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title_short Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
title_sort synthesis of 1,2-aminoalcohols through enantioselective aminoallylation of ketones by cu-catalyzed reductive coupling
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8384047/
https://www.ncbi.nlm.nih.gov/pubmed/34347500
http://dx.doi.org/10.1021/acs.orglett.1c02258
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