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...

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Bibliographic Details
Published in:New Journal of Chemistry
Main Authors: Aissa, Rim, Guezane-Lakoud, Samia, Kolodziej, Emilie, Toffano, Martial, Aribi-Zouioueche, Louisa
Other Authors: 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
Language:English
Published: HAL CCSD 2019
Subjects:
[CHIM.ORGA]Chemical Sciences/Organic chemistry
[CHIM.CATA]Chemical Sciences/Catalysis
Antarc*
Antarctica
Online Access: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
Description
Summary: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.

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