Abstract:
Diastereoselective synthesis of racemic and enantiopure 3-aryl-5-ethyl-1,4,2-oxazaphosphorines, including those bearing phenolic hydroxyl groups in the exocyclic aromatic fragment, was implemented by the reaction of imines derived from (±)-and (R)-(−)-2-aminobutan-1-ol and (hydroxy)benzaldehydes with triethyl phosphite and trifluoroacetic acid, followed by the one-pot dealkylation of the intermediate esters.
Citation:
K. E. Metlushka, D. N. Sadkova, K. A. Nikitina, Z. R. Yamaleeva, K. A. Ivshin, O. N. Kataeva, V. A. Alfonsov, “A new synthetic route to chiral 3-aryl-5-ethyl-1,4,2-oxazaphosphorines”, Mendeleev Commun., 28:6 (2018), 579–581
Linking options:
https://www.mathnet.ru/eng/mendc1841
https://www.mathnet.ru/eng/mendc/v28/i6/p579
This publication is cited in the following 5 articles:
K. E. Metlushka, R. G. Zinnatullin, K. A. Nikitina, E. K. Badeeva, “Chiral 2-Oxo-1,4,2-oxazaphosphorinanes: Synthesis, Structure, and Applications (A Review)”, Russ J Gen Chem, 93:9 (2023), 2237
K. E. Metlushka, R. G. Zinnatullin, K. A. Nikitina, E. K. Badeeva, “Chiral 2-oxo-1,4,2-oxazaphosphorinanes: synthesis, structure and applications (a review)”, Žurnal obŝej himii, 93:9 (2023), 1365
R. G. Zinnatullin, E. K. Badeeva, K. A. Nikitina, K. A. Ivshin, O. N. Kataeva, K. E. Metlushka, “Synthesis of Chiral 1,4,2-Oxazaphosphorinanes Bearing Pyridyl Substituents”, Russ J Gen Chem, 92:12 (2022), 2631
R. G. Zinnatullin, K. A. Nikitina, E. K. Badeeva, K. E. Metlushka, “New chiral 1,4,2-oxazaphosphorinanes bearing a free hydroxy group”, Russ Chem Bull, 70:7 (2021), 1383
O. I. Kolodiazhnyi, “Stereochemistry, mechanisms and applications of electrophilic reactions of organophosphorus compounds”, Russian Chem. Reviews, 89:5 (2020), 537–572
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