Synthesis of functionalized organophosphorus analogs of α- and β-alanine

Synthesis of functionalized organophosphorus analogs of α- and β-alanine Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 11, Pages: 3410-3421 Pages count : 12 DOI: 10.1007/s11172-024-4458-5

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	M. V. Lomonosov Moscow State University, Chemical Department, Build. 3, 1 Leninskiye Gory, 119991, Moscow, Russian Federation

Convenient syntheses of organophosphorus analogs of α- and β-alanine containing functionalized phosphonous and phosphinic acid moieties based on readily available trimethylsilyl esters of trivalent phosphorus acids have been developed. Nucleophilic addition of bis(trimethylsiloxy)phosphine to trimethylsilyl acrylates or α-(acetylamino)-acrylates proceeds regioselectively to give [2-(trimethylsiloxycarbonyl)ethyl]phosphonites, the subsequent functionalization of which affords various derivatives of the target acids. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.

Bubnov Y.N. , Prishchenko A.A. , Livantsov M.V. , Novikova O.P. , Livantsova L.I. , Baranin S.V.
Synthesis of functionalized organophosphorus analogs of α- and β-alanine
Russian Chemical Bulletin. 2024. V.73. N11. P.3410-3421. DOI: 10.1007/s11172-024-4458-5 WOS Scopus OpenAlex

≡ Web of science:	WOS:001397205100009
≡ Scopus:	2-s2.0-85218240968
≡ OpenAlex:	W4406318104