Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions

[Image: see text] The asymmetric α-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammo...

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Autores principales: Stockhammer, Lotte, Weinzierl, David, Bögl, Thomas, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8353620/
https://www.ncbi.nlm.nih.gov/pubmed/34319102
http://dx.doi.org/10.1021/acs.orglett.1c02256
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author Stockhammer, Lotte
Weinzierl, David
Bögl, Thomas
Waser, Mario
author_facet Stockhammer, Lotte
Weinzierl, David
Bögl, Thomas
Waser, Mario
author_sort Stockhammer, Lotte
collection PubMed
description [Image: see text] The asymmetric α-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated α-chlorinated ester derivative to prevent epimerization, thus allowing for enantioselectivities of up to e.r. 99:1.
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spelling pubmed-83536202021-08-10 Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions Stockhammer, Lotte Weinzierl, David Bögl, Thomas Waser, Mario Org Lett [Image: see text] The asymmetric α-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated α-chlorinated ester derivative to prevent epimerization, thus allowing for enantioselectivities of up to e.r. 99:1. American Chemical Society 2021-07-28 2021-08-06 /pmc/articles/PMC8353620/ /pubmed/34319102 http://dx.doi.org/10.1021/acs.orglett.1c02256 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 Stockhammer, Lotte
Weinzierl, David
Bögl, Thomas
Waser, Mario
Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title_full Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title_fullStr Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title_full_unstemmed Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title_short Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
title_sort enantioselective α-chlorination reactions of in situ generated c1 ammonium enolates under base-free conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8353620/
https://www.ncbi.nlm.nih.gov/pubmed/34319102
http://dx.doi.org/10.1021/acs.orglett.1c02256
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