Home / Publications / Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides

Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides

Anton Sergeevich Abel 1
Anton Sergeevich Abel
, 
Alexei Dmitrievich Averin 1
Alexei Dmitrievich Averin
, 
Evgenii Nikolaevich Savelyev 2
Evgenii Nikolaevich Savelyev
,  ,  , 
10.1016/j.mencom.2017.11.003
Published 2017-10-30
Communication , Volume 27, Issue 6, 550-552
9
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Abel A. S. et al. Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 550-552.
GOST all authors (up to 50) Copy
Abel A. S., Averin A. D., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 550-552.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.11.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.003
TI - Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides
T2 - Mendeleev Communications
AU - Abel, Anton Sergeevich
AU - Averin, Alexei Dmitrievich
AU - Savelyev, Evgenii Nikolaevich
AU - Orlinson, Boris Semionovich
AU - Novakov, Ivan Aleksandrovich
AU - Beletskaya, Irina Petrovna
PY - 2017
DA - 2017/10/30
PB - Mendeleev Communications
SP - 550-552
IS - 6
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Abel,
author = {Anton Sergeevich Abel and Alexei Dmitrievich Averin and Evgenii Nikolaevich Savelyev and Boris Semionovich Orlinson and Ivan Aleksandrovich Novakov and Irina Petrovna Beletskaya},
title = {Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.003},
number = {6},
pages = {550--552},
doi = {10.1016/j.mencom.2017.11.003}
}
MLA
Cite this
MLA Copy
Abel, Anton Sergeevich, et al. “Phosphine-catalyzed [3 + 2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides.” Mendeleev Communications, vol. 27, no. 6, Oct. 2017, pp. 550-552. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.003.

Abstract

Triphenylphosphine-catalyzed [3 + 2] cycloaddition between ethyl buta-2,3-dienoate and adamantane-containing N-substituted maleimides affords substituted bicyclic succinimides in excellent yields.

References

1.
Chiral phosphines in nucleophilic organocatalysis
Xiao Y., Sun Z., Guo H., Kwon O.
Beilstein Journal of Organic Chemistry, 2014
5.
2-Phospha[3]ferrocenophanes with Planar Chirality: Synthesis and Use in Enantioselective Organocatalytic [3 + 2] Cyclizations
Voituriez A., Panossian A., Fleury-Brégeot N., Retailleau P., Marinetti A.
Journal of the American Chemical Society, 2008
16.
F. Tamanoi, O. Kwon, M. Watanabe and H. Fiji, Patent WO 2007111948 A2, 2007.
18.
Design, synthesis, and biological activity of a novel series of 2,5-disubstituted furans/pyrroles as HIV-1 fusion inhibitors targeting gp41
Jiang S., Tala S.R., Lu H., Zou P., Avan I., Ibrahim T.S., Abo-Dya N.E., Abdelmajeid A., Debnath A.K., Katritzky A.R.
Bioorganic and Medicinal Chemistry Letters, 2011
19.
10.1016/j.mencom.2017.11.003_bib0095
Stepanov
Zh. Org. Khim., 1966
20.
B. Gopalan, A. Thomas and D. M. Shah, Patent WO 2006090244, 2006.
21.
The Adamantyl Group in Medicinal Agents. I. Hypoglycemic N-Arylsulfonyl-N'-adamantylureas
Gerzon K., Krumkalns E.V., Brindle R.L., Marshall F.J., Root M.A.
Journal of Medicinal Chemistry, 1963
22.
Synthesis and antiviral activity of the hydrochlorides of alicyclic mono- and diamines
Novakov I.A., Kulev I.A., Radchenko S.S., Birznieks K.A., Boreko E.I., Vladyko G.V., Korobchenko L.V.
Pharmaceutical Chemistry Journal, 1987
23.
Tsedilin A.M., Fakhrutdinov A.N., Eremin D.B., Zalesskiy S.S., Chizhov A.O., Kolotyrkina N.G., Ananikov V.P.
Mendeleev Communications, 2015
24.
Synthesis of a homotrifunctional conjugation reagent based on maleimide chemistry
Farha O.K., Julius R.L., Hawthorne M.F.
Tetrahedron Letters, 2006