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Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base

Kristina Aleksandrovna Nikitina 1
Kristina Aleksandrovna Nikitina
, 
Kirill Evgenievich Metlushka 1, 2
Kirill Evgenievich Metlushka
, 
Dilyara Nurgalievna Sadkova 1
Dilyara Nurgalievna Sadkova
, 
Liliya Nailevna Shaimardanova 1
Liliya Nailevna Shaimardanova
, 
Vladimir Alekseevich Alfonsov 1
Vladimir Alekseevich Alfonsov
10.1016/j.mencom.2016.09.009
Published 2016-09-08
Communication , Volume 26, Issue 5, 395-396
5
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Nikitina K. A. et al. Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base // Mendeleev Communications. 2016. Vol. 26. No. 5. pp. 395-396.
GOST all authors (up to 50) Copy
Nikitina K. A., Metlushka K. E., Sadkova D. N., Shaimardanova L. N., Alfonsov V. A. Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base // Mendeleev Communications. 2016. Vol. 26. No. 5. pp. 395-396.
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TY - JOUR
DO - 10.1016/j.mencom.2016.09.009
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.009
TI - Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base
T2 - Mendeleev Communications
AU - Nikitina, Kristina Aleksandrovna
AU - Metlushka, Kirill Evgenievich
AU - Sadkova, Dilyara Nurgalievna
AU - Shaimardanova, Liliya Nailevna
AU - Alfonsov, Vladimir Alekseevich
PY - 2016
DA - 2016/09/08
PB - Mendeleev Communications
SP - 395-396
IS - 5
VL - 26
ER -
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@article{2016_Nikitina,
author = {Kristina Aleksandrovna Nikitina and Kirill Evgenievich Metlushka and Dilyara Nurgalievna Sadkova and Liliya Nailevna Shaimardanova and Vladimir Alekseevich Alfonsov},
title = {Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base},
journal = {Mendeleev Communications},
year = {2016},
volume = {26},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.009},
number = {5},
pages = {395--396},
doi = {10.1016/j.mencom.2016.09.009}
}
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Nikitina, Kristina Aleksandrovna, et al. “Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base.” Mendeleev Communications, vol. 26, no. 5, Sep. 2016, pp. 395-396. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.009.

Abstract

A diastereoselective (de 80–92%) synthesis of α-amino phosphonates was accomplished by reaction of diethyl phosphite sodium salt with 3-R-1-phenyl-2,3-dihydro-1H-naphth[1,2-e]-[1,3]oxazines being the products of aminoacetalization of aldehydes with 1-(α-aminobenzyl)-2-naphthol (Betti base).

References

1.
10.1016/j.mencom.2016.09.009_bib0005
Aminophosphonic and Aminophosphinic Acids, 2000
2.
10.1016/j.mencom.2016.09.009_bib0010
Kukhar
2009
3.
The Betti base: the awakening of a sleeping beauty
Cardellicchio C., Capozzi M.A., Naso F.
Tetrahedron Asymmetry, 2010
5.
Stereoelectronic effects in ring-chain tautomerism of 1,3-diarylnaphth[1,2-e][1,3]oxazines and 3-alkyl-1-arylnaphth[1,2-e][1,3]oxazines.
Szatmári I., Martinek T.A., Lázár L., Koch A., Kleinpeter E., Neuvonen K., Fülöp F.
Journal of Organic Chemistry, 2004
6.
1-(α-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α-Aminophosphonic Acids
Metlushka K., Kashemirov B., Zheltukhin V., Sadkova D., Büchner B., Hess C., Kataeva O., McKenna C., Alfonsov V.
Chemistry - A European Journal, 2009
7.
Diastereoselective synthesis of α-aminoalkylphosphonic acid derivatives of Betti base
Metlushka K.E., Sadkova D.N., Shaimardanova L.N., Nikitina K.A., Tufatullin A.I., Kataeva O.N., Alfonsov V.A.
Russian Chemical Bulletin, 2014
9.
An update on the stereoselective synthesis of α-aminophosphonic acids and derivatives
Ordóñez M., Viveros-Ceballos J.L., Cativiela C., Sayago F.J.
Tetrahedron, 2015