Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity

• 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 (UBMA), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS), 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.science/hal-02359964; https://hal.science/hal-02359964/document; https://hal.science/hal-02359964/file/NJC2019%20Word%20HAL.pdf; https://doi.org/10.1039/c8nj06235h

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.