Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity
International audience New bis(α-aminophosphonates) were directly prepared with high diastereoselectivity by lipase catalytic promiscuity in the presence of immobilized Candida antarctica lipase. We focused on the multi-component Kabachnik–Fields reaction using various aldehydes, benzidine, and diet...
Published in: | New Journal of Chemistry |
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ftccsdartic:oai:HAL:hal-02359964v1 2023-05-15T13:31:10+02:00 Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity Aissa, Rim Guezane-Lakoud, Samia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa Université Badji Mokhtar - Annaba Annaba (UBMA) Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO) Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) Centre National de la Recherche Scientifique (CNRS) Université Paris-Saclay 2019 https://hal.archives-ouvertes.fr/hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964/document https://hal.archives-ouvertes.fr/hal-02359964/file/NJC2019%20Word%20HAL.pdf https://doi.org/10.1039/c8nj06235h en eng HAL CCSD Royal Society of Chemistry info:eu-repo/semantics/altIdentifier/doi/10.1039/c8nj06235h hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964/document https://hal.archives-ouvertes.fr/hal-02359964/file/NJC2019%20Word%20HAL.pdf doi:10.1039/c8nj06235h info:eu-repo/semantics/OpenAccess ISSN: 1144-0546 EISSN: 1369-9261 New Journal of Chemistry https://hal.archives-ouvertes.fr/hal-02359964 New Journal of Chemistry, Royal Society of Chemistry, 2019, 43 (21), pp.8153-8159. ⟨10.1039/c8nj06235h⟩ [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis info:eu-repo/semantics/article Journal articles 2019 ftccsdartic https://doi.org/10.1039/c8nj06235h 2022-01-09T00:16:01Z International audience New bis(α-aminophosphonates) were directly prepared with high diastereoselectivity by lipase catalytic promiscuity in the presence of immobilized Candida antarctica lipase. We focused on the multi-component Kabachnik–Fields reaction using various aldehydes, benzidine, and diethylphosphite in one pot. The reaction proceeded with short reaction times with good to excellent yields. The CAL-B was easily recovered and reused several times. A total diastereoselectivity was observed for bis(α-aminophosphonates) 4a, 4c, 4h, 4i, 4k and was high for 4b, 4f and 4j. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) New Journal of Chemistry 43 21 8153 8159 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
[CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis |
spellingShingle |
[CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis Aissa, Rim Guezane-Lakoud, Samia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
topic_facet |
[CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis |
description |
International audience New bis(α-aminophosphonates) were directly prepared with high diastereoselectivity by lipase catalytic promiscuity in the presence of immobilized Candida antarctica lipase. We focused on the multi-component Kabachnik–Fields reaction using various aldehydes, benzidine, and diethylphosphite in one pot. The reaction proceeded with short reaction times with good to excellent yields. The CAL-B was easily recovered and reused several times. A total diastereoselectivity was observed for bis(α-aminophosphonates) 4a, 4c, 4h, 4i, 4k and was high for 4b, 4f and 4j. |
author2 |
Université Badji Mokhtar - Annaba Annaba (UBMA) Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO) Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) Centre National de la Recherche Scientifique (CNRS) Université Paris-Saclay |
format |
Article in Journal/Newspaper |
author |
Aissa, Rim Guezane-Lakoud, Samia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa |
author_facet |
Aissa, Rim Guezane-Lakoud, Samia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa |
author_sort |
Aissa, Rim |
title |
Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
title_short |
Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
title_full |
Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
title_fullStr |
Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
title_full_unstemmed |
Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
title_sort |
diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity |
publisher |
HAL CCSD |
publishDate |
2019 |
url |
https://hal.archives-ouvertes.fr/hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964/document https://hal.archives-ouvertes.fr/hal-02359964/file/NJC2019%20Word%20HAL.pdf https://doi.org/10.1039/c8nj06235h |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1144-0546 EISSN: 1369-9261 New Journal of Chemistry https://hal.archives-ouvertes.fr/hal-02359964 New Journal of Chemistry, Royal Society of Chemistry, 2019, 43 (21), pp.8153-8159. ⟨10.1039/c8nj06235h⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1039/c8nj06235h hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964 https://hal.archives-ouvertes.fr/hal-02359964/document https://hal.archives-ouvertes.fr/hal-02359964/file/NJC2019%20Word%20HAL.pdf doi:10.1039/c8nj06235h |
op_rights |
info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.1039/c8nj06235h |
container_title |
New Journal of Chemistry |
container_volume |
43 |
container_issue |
21 |
container_start_page |
8153 |
op_container_end_page |
8159 |
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1766016459258986496 |