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Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent

[Image: see text] A highly efficient enantioselective α-nitrogenation method of α,α-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2-diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresp...

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Autores principales: Torregrosa-Chinillach, Alejandro, Carral-Menoyo, Asier, Gómez-Bengoa, Enrique, Chinchilla, Rafael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639010/
https://www.ncbi.nlm.nih.gov/pubmed/36283071
http://dx.doi.org/10.1021/acs.joc.2c01919
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author Torregrosa-Chinillach, Alejandro
Carral-Menoyo, Asier
Gómez-Bengoa, Enrique
Chinchilla, Rafael
author_facet Torregrosa-Chinillach, Alejandro
Carral-Menoyo, Asier
Gómez-Bengoa, Enrique
Chinchilla, Rafael
author_sort Torregrosa-Chinillach, Alejandro
collection PubMed
description [Image: see text] A highly efficient enantioselective α-nitrogenation method of α,α-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2-diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding α,α-disubstituted α-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through the calculation of green metrics, such as EcoScale and E-factor. In addition, theoretical calculations have been used to justify the obtained enantioselectivity sense.
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spelling pubmed-96390102022-11-08 Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent Torregrosa-Chinillach, Alejandro Carral-Menoyo, Asier Gómez-Bengoa, Enrique Chinchilla, Rafael J Org Chem [Image: see text] A highly efficient enantioselective α-nitrogenation method of α,α-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2-diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding α,α-disubstituted α-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through the calculation of green metrics, such as EcoScale and E-factor. In addition, theoretical calculations have been used to justify the obtained enantioselectivity sense. American Chemical Society 2022-10-25 2022-11-04 /pmc/articles/PMC9639010/ /pubmed/36283071 http://dx.doi.org/10.1021/acs.joc.2c01919 Text en © 2022 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 Torregrosa-Chinillach, Alejandro
Carral-Menoyo, Asier
Gómez-Bengoa, Enrique
Chinchilla, Rafael
Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title_full Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title_fullStr Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title_full_unstemmed Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title_short Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
title_sort organocatalytic enantioselective α-nitrogenation of α,α-disubstituted aldehydes in the absence of a solvent
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639010/
https://www.ncbi.nlm.nih.gov/pubmed/36283071
http://dx.doi.org/10.1021/acs.joc.2c01919
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