Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis

[Image: see text] An operationally simple Knoevenagel condensation/asymmetric epoxidation/domino ring-opening esterification (DROE) approach has been disclosed to successfully access a good variety of (R)- and (S)-α-arylglycine esters from commercially available aldehydes, phenylsulfonyl acetonitril...

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Autores principales: Battaglia, Vincenzo, Meninno, Sara, Pellegrini, Andrea, Mazzanti, Andrea, Lattanzi, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353036/
https://www.ncbi.nlm.nih.gov/pubmed/37382588
http://dx.doi.org/10.1021/acs.orglett.3c01736
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author Battaglia, Vincenzo
Meninno, Sara
Pellegrini, Andrea
Mazzanti, Andrea
Lattanzi, Alessandra
author_facet Battaglia, Vincenzo
Meninno, Sara
Pellegrini, Andrea
Mazzanti, Andrea
Lattanzi, Alessandra
author_sort Battaglia, Vincenzo
collection PubMed
description [Image: see text] An operationally simple Knoevenagel condensation/asymmetric epoxidation/domino ring-opening esterification (DROE) approach has been disclosed to successfully access a good variety of (R)- and (S)-α-arylglycine esters from commercially available aldehydes, phenylsulfonyl acetonitrile, cumyl hydroperoxide, anilines, and readily available Cinchona alkaloid-based catalysts using a single solvent and reaction vessel. DFT calculations performed on the key asymmetric epoxidation showed the importance of cooperative H-bonding interactions in affecting the stereocontrol.
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spelling pubmed-103530362023-07-19 Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis Battaglia, Vincenzo Meninno, Sara Pellegrini, Andrea Mazzanti, Andrea Lattanzi, Alessandra Org Lett [Image: see text] An operationally simple Knoevenagel condensation/asymmetric epoxidation/domino ring-opening esterification (DROE) approach has been disclosed to successfully access a good variety of (R)- and (S)-α-arylglycine esters from commercially available aldehydes, phenylsulfonyl acetonitrile, cumyl hydroperoxide, anilines, and readily available Cinchona alkaloid-based catalysts using a single solvent and reaction vessel. DFT calculations performed on the key asymmetric epoxidation showed the importance of cooperative H-bonding interactions in affecting the stereocontrol. American Chemical Society 2023-06-29 /pmc/articles/PMC10353036/ /pubmed/37382588 http://dx.doi.org/10.1021/acs.orglett.3c01736 Text en © 2023 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 Battaglia, Vincenzo
Meninno, Sara
Pellegrini, Andrea
Mazzanti, Andrea
Lattanzi, Alessandra
Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title_full Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title_fullStr Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title_full_unstemmed Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title_short Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
title_sort single-flask enantioselective synthesis of α-amino acid esters by organocatalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353036/
https://www.ncbi.nlm.nih.gov/pubmed/37382588
http://dx.doi.org/10.1021/acs.orglett.3c01736
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