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Enamine-based synthesis of functionalized aminoalkyl compounds bearing 3-, 4- or 5-coordinated phosphorus atom Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2024, Volume: 73, Number: 7, Pages: 1953-1961 Pages count : 9 DOI: 10.1007/s11172-024-4314-7
Authors Bubnov Yu.N. 1,2 , Prishchenko A.A. 3 , Livantsov M.V. 3 , Novikova O.P. 3 , Livantsova L.I. 3 , Baranin S.V. 2
Affiliations
1 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Build. 1, 28 ul. Vavilova, 119991, Moscow, Russian Federation
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
3 Chemical Department, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskiye Gory, 119991, Moscow, Russian Federation

Abstract: A convenient synthesis of functionalized aminoalkyl organophosphorus compounds bearing 3-, 4- or 5-coordinated phosphorus atom is based on readily available enamines and trivalent phosphorus acid esters. Radical addition of bis(trimethylsiloxy)phosphine to enamines proceeds regioselectively to give aminoalkylphosphonites, and their subsequent functionalization affords various derivatives of the target acids. The nucleophilic addition of hydrospirophosphorane to enamines also proceeds regioselectively to furnish α-aminoalkyl spirophosphoranes containing five-coordinated phosphorus atom. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.
Cite: Bubnov Y.N. , Prishchenko A.A. , Livantsov M.V. , Novikova O.P. , Livantsova L.I. , Baranin S.V.
Enamine-based synthesis of functionalized aminoalkyl compounds bearing 3-, 4- or 5-coordinated phosphorus atom
Russian Chemical Bulletin. 2024. V.73. N7. P.1953-1961. DOI: 10.1007/s11172-024-4314-7 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001303930000007
≡ Scopus: 2-s2.0-85202770628
≡ OpenAlex: W4402103162
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