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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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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. |
format | Online Article Text |
id | pubmed-9639010 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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