Home / Publications / Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids

Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids

Angelina Nikolaevna Kravchenko 1
Angelina Nikolaevna Kravchenko
Konstantin Yur'evich Chegaev 1
Konstantin Yur'evich Chegaev
Il'ya Evgen'evich Chikunov 1
Il'ya Evgen'evich Chikunov
Pavel Alekseevich Belyakov 1
Pavel Alekseevich Belyakov
Elena Yulianovna Maksareva 1
Elena Yulianovna Maksareva
Konstantin Alexandrovich Lyssenko
Oleg Vasilevich Lebedev 1
Oleg Vasilevich Lebedev
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
Published 2003-12-26
CommunicationVolume 13, Issue 6, 269-271
16
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kravchenko A. N. et al. Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids // Mendeleev Communications. 2003. Vol. 13. No. 6. pp. 269-271.
GOST all authors (up to 50) Copy
Kravchenko A. N., Chegaev K. Y., Chikunov I. E., Belyakov P. A., Maksareva E. Y., Lyssenko K. A., Lebedev O. V., Makhova N. N. Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids // Mendeleev Communications. 2003. Vol. 13. No. 6. pp. 269-271.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2003v013n06ABEH001802
UR - https://mendcomm.colab.ws/publications/10.1070/MC2003v013n06ABEH001802
TI - Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids
T2 - Mendeleev Communications
AU - Kravchenko, Angelina Nikolaevna
AU - Chegaev, Konstantin Yur'evich
AU - Chikunov, Il'ya Evgen'evich
AU - Belyakov, Pavel Alekseevich
AU - Maksareva, Elena Yulianovna
AU - Lyssenko, Konstantin Alexandrovich
AU - Lebedev, Oleg Vasilevich
AU - Makhova, Nina Nikolaevna
PY - 2003
DA - 2003/12/26
PB - Mendeleev Communications
SP - 269-271
IS - 6
VL - 13
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2003_Kravchenko,
author = {Angelina Nikolaevna Kravchenko and Konstantin Yur'evich Chegaev and Il'ya Evgen'evich Chikunov and Pavel Alekseevich Belyakov and Elena Yulianovna Maksareva and Konstantin Alexandrovich Lyssenko and Oleg Vasilevich Lebedev and Nina Nikolaevna Makhova},
title = {Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids},
journal = {Mendeleev Communications},
year = {2003},
volume = {13},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2003v013n06ABEH001802},
number = {6},
pages = {269--271},
doi = {10.1070/MC2003v013n06ABEH001802}
}
MLA
Cite this
MLA Copy
Kravchenko, Angelina Nikolaevna, et al. “Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids.” Mendeleev Communications, vol. 13, no. 6, Dec. 2003, pp. 269-271. https://mendcomm.colab.ws/publications/10.1070/MC2003v013n06ABEH001802.

Abstract

The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-α-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined for three stereoisomers by X-ray diffraction analysis.

References

2.
Multifunctionalized Glycolurils
Pryor K.E., Rebek J.
Organic Letters, 1999
3.
Methods of synthesis of nitrogen-containing heterocycles using ureas and related compounds
5.
Kostyanovsky R.G., Lyssenko K.A., Kadorkina G.K., Lebedev O.V., Kravchenko A.N., Chervin I.I., Kostyanovsky V.R.
Mendeleev Communications, 1998
6.
Chegaev K.Y., Kravchenko A.N., Lebedev O.V., Strelenko Y.A.
Mendeleev Communications, 2001
7.
Gazieva G.A., Lyssenko K.A., Gaziev R.G., Kravchenko A.N., Lebedev O.V., Zhulin V.M.
Mendeleev Communications, 2001
8.
Gazieva G.A., Kravchenko A.N., Lebedev O.V., Lyssenko K.A., Dekaprilevich M.O., Men'shov V.M., Strelenko Y.A., Makhova N.N.
Mendeleev Communications, 2001
9.
10.1070/MC2003v013n06ABEH001802_bib6
Kravchenko
Izv. Akad. Nauk, Ser. Khim., 2003
12.
Synthese und Eigenschaften füngliedriger cyclischer Harnstoffe
Petersen H.
European Journal of Organic Chemistry, 1969
13.
A pH-dependent cyanate reactivity model: application to preparative N-carbamoylation of amino acids
Taillades J., Boiteau L., Beuzelin I., Lagrille O., Biron J., Vayaboury W., Vandenabeele-Trambouze O., Giani O., Commeyras A.
Journal of the Chemical Society Perkin Transactions 2, 2001
14.
10.1070/MC2003v013n06ABEH001802_bib11
Pechenkin
Izv. Tomsk. Politekh. Inst., 1974