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Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst
A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averagin...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9413694/ https://www.ncbi.nlm.nih.gov/pubmed/36014353 http://dx.doi.org/10.3390/molecules27165113 |
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author | Summa, Assunta Scafato, Patrizia Belviso, Sandra Monaco, Guglielmo Zanasi, Riccardo Longhi, Giovanna Abbate, Sergio Superchi, Stefano |
author_facet | Summa, Assunta Scafato, Patrizia Belviso, Sandra Monaco, Guglielmo Zanasi, Riccardo Longhi, Giovanna Abbate, Sergio Superchi, Stefano |
author_sort | Summa, Assunta |
collection | PubMed |
description | A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign the absolute configuration of a benzylic stereocenter in the presence of a chiral binaphthyl moiety. The 1,1′-binaphthylazepine tetrazole and the nitrile its immediate synthetic precursor, have been preliminarily tested as chiral organocatalysts in the asymmetric intramolecular oxa-Michael cyclization of 2-hydroxy chalcones for the synthesis of chiral flavanones obtaining low enantioselectivity. |
format | Online Article Text |
id | pubmed-9413694 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-94136942022-08-27 Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst Summa, Assunta Scafato, Patrizia Belviso, Sandra Monaco, Guglielmo Zanasi, Riccardo Longhi, Giovanna Abbate, Sergio Superchi, Stefano Molecules Article A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign the absolute configuration of a benzylic stereocenter in the presence of a chiral binaphthyl moiety. The 1,1′-binaphthylazepine tetrazole and the nitrile its immediate synthetic precursor, have been preliminarily tested as chiral organocatalysts in the asymmetric intramolecular oxa-Michael cyclization of 2-hydroxy chalcones for the synthesis of chiral flavanones obtaining low enantioselectivity. MDPI 2022-08-11 /pmc/articles/PMC9413694/ /pubmed/36014353 http://dx.doi.org/10.3390/molecules27165113 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Summa, Assunta Scafato, Patrizia Belviso, Sandra Monaco, Guglielmo Zanasi, Riccardo Longhi, Giovanna Abbate, Sergio Superchi, Stefano Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title | Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title_full | Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title_fullStr | Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title_full_unstemmed | Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title_short | Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst |
title_sort | synthesis and stereochemical characterization of a novel chiral α-tetrazole binaphthylazepine organocatalyst |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9413694/ https://www.ncbi.nlm.nih.gov/pubmed/36014353 http://dx.doi.org/10.3390/molecules27165113 |
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