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Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran

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Shmatova O. I., Nenajdenko V. G. Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 57-58.
GOST all authors (up to 50) Copy
Shmatova O. I., Nenajdenko V. G. Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 57-58.
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TY - JOUR
DO - 10.1016/j.mencom.2019.01.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.018
TI - Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran
T2 - Mendeleev Communications
AU - Shmatova, Olga I
AU - Nenajdenko, Valentin Georgievich
PY - 2018
DA - 2018/01/28
PB - Mendeleev Communications
SP - 57-58
IS - 1
VL - 29
ER -
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@article{2018_Shmatova,
author = {Olga I Shmatova and Valentin Georgievich Nenajdenko},
title = {Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.018},
number = {1},
pages = {57--58},
doi = {10.1016/j.mencom.2019.01.018}
}
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Shmatova, Olga I., and Valentin Georgievich Nenajdenko. “Diastereoselective vinylogous Mannich reaction of perfluoroalkylated cyclic imines with 2-trimethylsilyloxyfuran.” Mendeleev Communications, vol. 29, no. 1, Jan. 2018, pp. 57-58. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.018.

Abstract

The reaction between 2-trimethylsilyloxyfuran and perfluoroalkylated cyclic ketimines with different ring sizes affords 5-(2-perfluoroalkyl-1-azacycloalk-2-yl)furan-2(5H)-ones in yields up to 89% and with excellent rel-(R,R)-diastereoselectivity.

References

1.
Fluorinated amino acids: compatibility with native protein structures and effects on protein–protein interactions
Salwiczek M., Nyakatura E.K., Gerling U.I., Ye S., Koksch B.
Chemical Society Reviews, 2012
3.
Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)
Wang J., Sánchez-Roselló M., Aceña J.L., del Pozo C., Sorochinsky A.E., Fustero S., Soloshonok V.A., Liu H.
Chemical Reviews, 2013
5.
Aromatic Trifluoromethylation with Metal Complexes
Tomashenko O.A., Grushin V.V.
Chemical Reviews, 2011
6.
Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective
Shibata N., Matsnev A., Cahard D.
Beilstein Journal of Organic Chemistry, 2010
8.
Aromatic trifluoromethylation catalytic in copper.
Oishi M., Kondo H., Amii H.
Chemical Communications, 2009
9.
Perfluoroalkylation with Organosilicon Reagents
Prakash G.K., Yudin A.K.
Chemical Reviews, 1997
10.
Kuvshinova S.S., Smol’yakov A.F., Vorobyeva D.V., Osipov S.N., Loginov D.A.
Mendeleev Communications, 2018
11.
Ivanova A.E., Burgart Y.V., Saloutin V.I., Orshanskaya Y.R., Zarubaev V.V.
Mendeleev Communications, 2018
12.
10.1016/j.mencom.2019.01.018_sbref0015a
Shevchenko
Synthesis, 2010
16.
Shmatova O.I., Shevchenko N.E., Balenkova E.S., Röschenthaler G., Nenajdenko V.G.
Mendeleev Communications, 2013
18.
Highly β‐Regioselective Friedel–Crafts Aminoalkylation of Pyrroles with Cyclic Perfluoroalkylated Imines
Shmatova O.I., Shevchenko N.E., Balenkova E.S., Röschenthaler G., Nenajdenko V.G.
European Journal of Organic Chemistry, 2013
19.
Kutovaya I.V., Shmatova O.I., Nenajdenko V.G.
Mendeleev Communications, 2018
21.
Synthetic Studies onPandanus Alkaloids: From Norpandamarilactonines to Pandamarilactonines, a Proof of Their Configurational Instability
Blanco P., Busqué F., de March P., Figueredo M., Font J., Sanfeliu E.
European Journal of Organic Chemistry, 2004
25.
Vinylogous Mannich reactions. Additions of trimethylsilyloxyfuran to fluorinated aldimines
Spanedda M.V., Ourévitch M., Crousse B., Bégué J., Bonnet-Delpon D.
Tetrahedron Letters, 2004
30.
10.1016/j.mencom.2019.01.018_bib0035
Frisch
Gaussian 03W, Revision B.05, 2003