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Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites
Тип публикации: Journal Article
Дата публикации: 2003-03-27
scimago Q4
wos Q3
БС2
SJR: 0.146
CiteScore: 2.3
Impact factor: 1.4
ISSN: 10427163, 10981071
General Chemistry
Краткое описание
The intramolecular version of nucleophilic additon of phosphites to imines was carried out for the first time taking as an example β-aldiminoalkylphosphites, formed from chlorophosphites and β-aldiminoalcohols [N-(benzylidene)-2-aminoethanol and R-(+)-N-(benzylidene)-2-aminobutanol-1]. In these reactions, stereoisomeric 1,4,2-oxazaphosphorines were obtained in good yields. R-(+)-N-(benzylidene)-2-aminobutanol-1 being used as a precursor, nucleophilic attack by P(III) atom on electrophilic C atom of the CN group proceeds stereospecifically with participation of only re-face of the two possible diastereotopic faces of the imine double bond to give the epimeric at phosphorus (3R,5R)-2-(β-chloroethyl)-2-oxo-3-phenyl-5-ethyl-1,4,2-oxazaphosphorines as precursors of nonracemic α-aminophosphonic acids. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:56–61, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10054
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Dimukhametov M. N. et al. Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites // Heteroatom Chemistry. 2003. Vol. 14. No. 1. pp. 56-61.
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Dimukhametov M. N., Bajandina E. V., Davydova E. Yu., Litvinov I. A., Gubaidullin A. T., Dobrynin A., Zyablikova T. A., Al'Fonsov V. A. Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites // Heteroatom Chemistry. 2003. Vol. 14. No. 1. pp. 56-61.
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TY - JOUR
DO - 10.1002/hc.10054
UR - https://doi.org/10.1002/hc.10054
TI - Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites
T2 - Heteroatom Chemistry
AU - Dimukhametov, Mudaris N.
AU - Bajandina, Eugenija V
AU - Davydova, Elena Yu
AU - Litvinov, I. A.
AU - Gubaidullin, Aidar T.
AU - Dobrynin, Alexey
AU - Zyablikova, Tatyana A
AU - Al'Fonsov, Vladimir A.
PY - 2003
DA - 2003/03/27
PB - Wiley
SP - 56-61
IS - 1
VL - 14
SN - 1042-7163
SN - 1098-1071
ER -
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@article{2003_Dimukhametov,
author = {Mudaris N. Dimukhametov and Eugenija V Bajandina and Elena Yu Davydova and I. A. Litvinov and Aidar T. Gubaidullin and Alexey Dobrynin and Tatyana A Zyablikova and Vladimir A. Al'Fonsov},
title = {Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites},
journal = {Heteroatom Chemistry},
year = {2003},
volume = {14},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/hc.10054},
number = {1},
pages = {56--61},
doi = {10.1002/hc.10054}
}
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Dimukhametov, Mudaris N., et al. “Stereoselective synthesis of 1,4,2‐oxazaphosphorines as precursors of chiral α‐aminophosphonic acids by intramolecular heterocyclization of β‐aldiminoalkylphosphites.” Heteroatom Chemistry, vol. 14, no. 1, Mar. 2003, pp. 56-61. https://doi.org/10.1002/hc.10054.