Home / Publications / Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes

Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes

Kristian Samvelovich Andriasov 1
Kristian Samvelovich Andriasov
Marina Gennadievna Eremenko 1
Marina Gennadievna Eremenko
Tamara Stepanovna Kuznetsova 1
Tamara Stepanovna Kuznetsova
Elena Borisovna Averina 1, 2
Elena Borisovna Averina
Published 2021-04-28
CommunicationVolume 31, Issue 3, 294-296
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Andriasov K. S. et al. Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 294-296.
GOST all authors (up to 50) Copy
Andriasov K. S., Sedenkova K. N., Eremenko M. G., Gloriozov I. P., Grishin Y. K., Kuznetsova T. S., Averina E. B. Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 294-296.
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TY - JOUR
DO - 10.1016/j.mencom.2021.04.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.005
TI - Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes
T2 - Mendeleev Communications
AU - Andriasov, Kristian Samvelovich
AU - Sedenkova, Kseniya N
AU - Eremenko, Marina Gennadievna
AU - Gloriozov, Igor Pavlovich
AU - Grishin, Yuri Konstantinovich
AU - Kuznetsova, Tamara Stepanovna
AU - Averina, Elena Borisovna
PY - 2021
DA - 2021/04/28
PB - Mendeleev Communications
SP - 294-296
IS - 3
VL - 31
ER -
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@article{2021_Andriasov,
author = {Kristian Samvelovich Andriasov and Kseniya N Sedenkova and Marina Gennadievna Eremenko and Igor Pavlovich Gloriozov and Yuri Konstantinovich Grishin and Tamara Stepanovna Kuznetsova and Elena Borisovna Averina},
title = {Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.005},
number = {3},
pages = {294--296},
doi = {10.1016/j.mencom.2021.04.005}
}
MLA
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Andriasov, Kristian Samvelovich, et al. “Direct oxidative functionalization of saturated dispiro-cyclopropanated bicyclo[3.3.1]nonanes.” Mendeleev Communications, vol. 31, no. 3, Apr. 2021, pp. 294-296. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.005.

Keywords

1,5-diketones
bicyclo[3.3.1]nonanes
Cyclopropanes
cyclopropyl ketones
methyl(trifluoromethyl)dioxirane
oxidation
ozone
ruthenium(VIII) oxide
spiro compounds

Abstract

Two dispiro[cyclopropane-1,3’-bicyclo[3.3.1]nonane-7′,1″-cyclopropanes] were treated with various oxidative systems. The conditions providing mono- or dioxidation of the CH2 groups neighbouring to spiro-annulated cyclopropane moieties to afford the corresponding mono- or diketones were found.

References

1.
Chemistry, Pharmacology, and Clinical Efficacy of the Chinese Nootropic Agent Huperzine A
Kozikowski A.P., Tückmantel W.
Accounts of Chemical Research, 1999
2.
Wickerols A and B: novel anti-influenza virus diterpenes produced by Trichoderma atroviride FKI-3849
Yamamoto T., Izumi N., Ui H., Sueki A., Masuma R., Nonaka K., Hirose T., Sunazuka T., Nagai T., Yamada H., Ōmura S., Shiomi K.
Tetrahedron, 2012
3.
Polycyclic polyprenylated acylphloroglucinols.
Ciochina R., Grossman R.B.
Chemical Reviews, 2006
5.
The Chemistry of the Polycyclic Polyprenylated Acylphloroglucinols
Richard J., Pouwer R.H., Chen D.Y.
Angewandte Chemie - International Edition, 2012
8.
Hydrodealkenylative C(sp 3 )–C(sp 2 ) bond fragmentation
Smaligo A.J., Swain M., Quintana J.C., Tan M.F., Kim D.A., Kwon O.
Science, 2019
9.
Enantioselective C–H Lactonization of Unactivated Methylenes Directed by Carboxylic Acids
Cianfanelli M., Olivo G., Milan M., Klein Gebbink R.J., Ribas X., Bietti M., Costas M.
Journal of the American Chemical Society, 2019
11.
Oxyfunctionalization of CH2-Group Activated by Adjacent Three-Membered Ring
Sedenkova K.N., Andriasov K.S., Kuznetsova T.S., Averina E.B.
Current Organic Synthesis, 2018
12.
On Inventing Reactions for Atom Economy
Trost B.M.
Accounts of Chemical Research, 2002
13.
Function-oriented synthesis, step economy, and drug design.
Wender P.A., Verma V.A., Paxton T.J., Pillow T.H.
Accounts of Chemical Research, 2007
14.
10.1016/j.mencom.2021.04.005_bib0070
Kozhushkov
Sci. Synth., 2009
15.
Beyond the Dimer and Trimer: Tetraspiro[2.1.2 5 .1.2 9 .1.2 13 .1 3 ] hexadecane‐1,3,5,7‐tetraone—the Cyclic Tetramer of Carbonylcyclopropane
Sedenkova K.N., Averina E.B., Grishin Y.K., Andriasov K.S., Stepanova S.A., Roznyatovsky V.A., Kutateladze A.G., Rybakov V.B., Albov D.V., Kuznetsova T.S., Zefirov N.S.
Chemistry - A European Journal, 2016
16.
Direct Oxidation of Cyclopropanated Cyclooctanes as a Synthetic Approach to Polycyclic Cyclopropyl Ketones
Sedenkova K.N., Andriasov K.S., Stepanova S.A., Gloriozov I.P., Grishin Y.K., Kuznetsova T.S., Averina E.B.
European Journal of Organic Chemistry, 2018
17.
Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes
Budynina E., Ivanov K., Sorokin I., Melnikov M.
Synthesis, 2017
18.
Dichotomy of Reductive Addition of Amines to Cyclopropyl Ketones vs Pyrrolidine Synthesis
Afanasyev O.I., Tsygankov A.A., Usanov D.L., Chusov D.
Organic Letters, 2016
20.
Brønsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition
Li J., Zhu S., Xu Q., Liu L., Yan S.
Organic and Biomolecular Chemistry, 2019
21.
10.1016/j.mencom.2021.04.005_bib0105
Krasutskii
J. Org. Chem. USSR (Engl. Transl.), 1984
22.
symm-Tetramethylenecyclooctane: En Route to Polyspirocycles
Averina E.B., Sedenkova K.N., Bakhtin S.G., Grishin Y.K., Kutateladze A.G., Roznyatovsky V.A., Rybakov V.B., Butov G.M., Kuznetsova T.S., Zefirov N.S.
Journal of Organic Chemistry, 2014
23.
Three-Membered-Ring-Based Molecular Architectures
de Meijere A., Kozhushkov S.I., Schill H.
Chemical Reviews, 2006