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

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Abstract

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.

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

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Publication details

The article was received on 10 Dec 2018, accepted on 21 Apr 2019 and first published on 14 May 2019


Article type: Paper
DOI: 10.1039/C8NJ06235H
New J. Chem., 2019, Advance Article

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

    R. Aissa, S. Guezane-Lakoud, E. Kolodziej, M. Toffano and L. Aribi-Zouioueche, New J. Chem., 2019, Advance Article , DOI: 10.1039/C8NJ06235H

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