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Issue 21, 2019
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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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Supplementary files

Article information


Submitted
10 Dec 2018
Accepted
21 Apr 2019
First published
14 May 2019

New J. Chem., 2019,43, 8153-8159
Article type
Paper

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, 43, 8153
DOI: 10.1039/C8NJ06235H

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