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Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane

Andrey Andreevich Mikhaylov 1
Andrey Andreevich Mikhaylov
, 
Petr Aleksandrovich Zhmurov 1
Petr Aleksandrovich Zhmurov
, 
Anastasia S Naumova 1
Anastasia S Naumova
, 
Yulia A Khoroshutina 1
Yulia A Khoroshutina
, 
Alexey Yu Sukhorukov 1
Alexey Yu Sukhorukov
, 
Sema Leibovich Ioffe 1
Sema Leibovich Ioffe
10.1016/j.mencom.2015.11.017
Published 2015-11-09
Communication , Volume 25, Issue 6, 449-451
8
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Mikhaylov A. A. et al. Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 449-451.
GOST all authors (up to 50) Copy
Mikhaylov A. A., Zhmurov P. A., Naumova A. S., Khoroshutina Y. A., Sukhorukov A. Yu., Ioffe S. L. Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 449-451.
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TY - JOUR
DO - 10.1016/j.mencom.2015.11.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.017
TI - Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane
T2 - Mendeleev Communications
AU - Mikhaylov, Andrey Andreevich
AU - Zhmurov, Petr Aleksandrovich
AU - Naumova, Anastasia S
AU - Khoroshutina, Yulia A
AU - Sukhorukov, Alexey Yu
AU - Ioffe, Sema Leibovich
PY - 2015
DA - 2015/11/09
PB - Mendeleev Communications
SP - 449-451
IS - 6
VL - 25
ER -
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@article{2015_Mikhaylov,
author = {Andrey Andreevich Mikhaylov and Petr Aleksandrovich Zhmurov and Anastasia S Naumova and Yulia A Khoroshutina and Alexey Yu Sukhorukov and Sema Leibovich Ioffe},
title = {Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.017},
number = {6},
pages = {449--451},
doi = {10.1016/j.mencom.2015.11.017}
}
MLA
Cite this
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Mikhaylov, Andrey Andreevich, et al. “Stereoselective synthesis of spirocyclic nitronates by SnCl4-promoted reaction of nitroalkenes with C-2 substituted 4-methylidene-1,3-dioxolane.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 449-451. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.017.

Abstract

SnCl4-promoted [4 + 2] cycloaddition of β-nitrostyrenes to 4-methylidene-1,3-dioxolane provides stereoselective synthesis of spirocyclic nitronates. 2-Nitrovinyl benzoate under the same conditions produces δ-substituted nitrodiene as a single E,E-isomer.

References

1.
10.1016/j.mencom.2015.11.017_sbref0005a
Ioffe
Nitrile Oxides Nitrones and Nitronates in Organic Synthesis. Novel Strategies in Synthesis, 2008
2.
Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes
Denmark S.E., Thorarensen A.
Chemical Reviews, 1996
3.
10.1016/j.mencom.2015.11.017_sbref0005c
Sukhorukov
Chem. Heterocycl. Compd., 2012, 48, 49., 2012
4.
10.1016/j.mencom.2015.11.017_sbref0005d
Bastrakov
Chem. Heterocycl. Compd., 2015,.51, 496., 2015
5.
Ozonation of benzotetrazine 1,3-dioxides. Facile synthesis of di(methoxycarbonyl)-1,2,3,4-tetrazine 1,3-dioxide
Klenov M.S., Churakov A.M., Strelenko Y.A., Ananyev I.V., Lyssenko K.A., Tartakovsky V.A.
Tetrahedron Letters, 2015
7.
An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy
Fershtat L.L., Epishina M.A., Kulikov A.S., Ovchinnikov I.V., Ananyev I.V., Makhova N.N.
Tetrahedron, 2015
8.
10.1016/j.mencom.2015.11.017_sbref0010a
Denmark
J. Am. Chem. Soc., 1999
10.
10.1016/j.mencom.2015.11.017_sbref0015a
Sukhorukov
Chem. Rev., 2011
11.
Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
Sukhorukov A.Y., Boyko Y.D., Ioffe S.L., Khomutova Y.A., Nelyubina Y.V., Tartakovsky V.A.
Journal of Organic Chemistry, 2011
12.
10.1016/j.mencom.2015.11.017_sbref0020a
Denmark
Tetrahedron, 1990
14.
trans-2-Phenylcyclohexanol. A powerful and readily available chiral auxiliary
Whitesell J.K., Chen H.H., Lawrence R.M.
Journal of Organic Chemistry, 1985
16.
First asymmetric synthesis of pyrrolizidine alkaloids, (+)-hyacinthacine B1 and (+)-B2
Sengoku T., Satoh Y., Oshima M., Takahashi M., Yoda H.
Tetrahedron, 2008
18.
10.1016/j.mencom.2015.11.017_sbref0040a
Gevorkyan
Chem. Heterocycl. Compd., 1991, 27, 27 (Khim. Geterotsikl. Soedin., 1991
20.
10.1016/j.mencom.2015.11.017_sbref0045a
Denmark
J. Org. Chem., 1997
21.
10.1016/j.mencom.2015.11.017_sbref0045b
Denmark
J. Org. Chem., 1997
23.
On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes
Attanasi O.A., Favi G., Filippone P., Forzato C., Giorgi G., Morganti S., Nitti P., Pitacco G., Rizzato E., Spinelli D., Valentin E.
Tetrahedron, 2006