Synthesis of 3-diethylphosphonoyl-2-hydroxy-prop-2-ylphosphonate and -phosphine oxide derivatives via the Pudovik reaction of diethyl 2-oxopropylphosphonate on the surface of Al2O3/KF

• Published in: Tetrahedron letters Vol. 68; pp. 152902 - 152904
• Main Authors: Varga, Petra R., Hägele, Gerhard, Keglevich, György
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.03.2021; Elsevier
• Subjects: 31P NMR features; Chemistry; Chemistry, Organic; Physical Sciences; Pudovik reaction; Science & Technology; Solid phase synthesis; α-Hydroxyphosphonates; 31P NMR features; α-Hydroxyphosphonates; Solid phase synthesis; Pudovik reaction; P-31 NMR features; alpha-Hydroxyphosphonates
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2021.152902

[Display omitted] •Synthesis of β-phosphonoyl-α-hydroxyphosphonates as a new family of compounds.•Solvent-free preparation on the surface of Al2O3/KF.•Stereospecific 3J(PC) couplings.•Conformational analysis. A series of dialkyl 3-diethylphosphonoyl-2-hydroxy-prop-2-ylphosphonates and a diphenylphosphine oxide, new representatives within the large family of α-hydroxyphosphonates, were prepared via the Pudovik reaction of the corresponding dialkyl phosphites or diphenylphosphine oxide with diethyl 2-oxopropylphosphonate on the surface of Al2O3/KF. The conformation of the α-hydroxy-ethylenebisphosphonate derivatives was established on the basis of stereospecific 3JPC constants.