Diastereoselective synthesis of novel 5-substituted morpholine-3-phosphonic acids: further exploitation of N-acyliminium intermediates |
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| Institution: | 1. Università del Piemonte Orientale “A. Avogadro”, Dipartimento di Scienze del Farmaco, Largo Donegani 2, I-28100 Novara, Italy;2. Università degli Studi dell’Insubria, Dipartimento di Scienza e Alta Tecnologia, Via Valleggio 11, I-22100 Como, Italy;3. Università degli Studi di Pavia, Dipartimento di Chimica, Via Taramelli 12, I-27100 Pavia, Italy;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Northern Border University, PO Box 840, Rafha 91911, Saudi Arabia;2. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt;3. Department of Pharmacology, Faculty of Veterinary Medicine, Zagazig University, Zagazig, Egypt;4. Department of Chemistry, Faculty of Arts and Science, Northern Border University, PO Box 840, Rafha 91911, Saudi Arabia;5. Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11284, Egypt;1. Laboratory for Medicinal Chemistry, Ghent University, Ottergemsesteenweg 460, B-9000 Ghent, Belgium;2. Laboratory for Pharmaceutical Microbiology, Ghent University, Ottergemsesteenweg 460, B-9000 Ghent, Belgium |
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| Abstract: | The first diastereoselective total synthesis of 5-substituted morpholine-3-phosphonic acids is reported. The principal feature of the synthesis is the introduction of a dimethyl phosphonate group into 5-substituted morpholin-3-ones. The procedure is based on the preparation of N-Boc-(S)-5-phenyl- and N-Boc-(S)-5-benzylmorpholin-3-one from l-phenylglycine and l-phenylalanine methyl esters, followed by the formation of the 3-methoxylated compounds and subsequent reaction with trimethyl phosphite in the presence of BF3·OEt2. Diastereoselectivity in the formation of cis-disubstituted products is in agreement with the nucleophilic addition to other methoxylated derivatives. |
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