Chemoenzymatic synthesis of chiral phosphonate derivatives of biological interest
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Date
2024
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Abstract
In the initial part, we detail the synthesis of a novel series of a- amino-phosphonate derivatives through an organocatalytic pathway, utilizing diphenylphosphinic acid and applying the Design of Experiment method. The Kabachnik-Fields reaction was employed under eco-friendly conditions, adhering to the principles of green chemistry. The successful synthesis of all derivatives underscores the efficiency of this methodology.The second part focuses on the design and synthesis of a-aminophosphonate derivatives, recognizing their pharmacological and chemical importance. The presence of 2-Hydroxymethyl-18-Crown-6 played a pivotal role in the synthesis. Furthermore, a comprehensive theoretical study, employing DFT and molecular docking, was conducted to elucidate the chemical reactivity and biological relevance of the synthesized molecules. The mentioned products were obtained with high yields under optimal conditions.In the last part we focus on the enantioselective deacylation of secondary benzylic acetates catalyzed by CAL-B as key pathway to easily access to enantiopure organophosphorus compounds. This reaction unfolded in a non-aqueous medium in the presence of DABCO as a crucial additive.The application of various spectroscopic methods, including 1H, 13C, and 31P NMR, along with mass spectrometry, was pivotal in establishing the structural characteristics of the synthesized compounds.