Abstract
Sodium benzeneselenolate adds regio- and stereoselectively to 3-(trimethylsilyl)prop-2-yn-amides to give (Z)-3-(phenylselanyl)prop-2-enamides.
References
G. Perin, E. J. Lenardão, R. G. Jacob, R. B. Panatieri, Chem. Rev., 2009, 109, 1277.
M. Palomba, L. Bagnoli, F. Marini, C. Santi, L. Sancineto, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 235.
B. Banerjee, M. Koketsu, Coord. Chem. Rev., 2017, 339, 104.
BR Pat. 102015005553; Chem. Abstrs., 2019, 170, 193057.
BR Pat. 102015032954; Chem. Abstrs., 2019, 170, 298792.
X. Ren, L. Zou, J. Lu, A. Holmgren, Free Radical Biol. Med., 2018, 127, 238.
G. K. Azad, R. S. Tomar, Mol. Biol. Rep., 2014, 41, 4865.
L. A. Tsoi, A. K. Patsaev, V. Zh. Ushanov, L. V. Vyaznikovtsev, Zh. Org. Khim. [Russ. J. Org. Chem.], 1984, 20, 2081 (in Russian).
D. Garía-López, M. G. Civit, C. M. Vogels, J. M. Ricart, S. A. Westcott, E. Fernández, J. J. Carbó, Catal. Sci. Technol., 2018, 8, 3617.
D. J. Knapton, T. Y. Meyer, J. Org. Chem., 2005, 70, 785.
S. Fujiwara, M. Toyofuku, H. Kuniyasu, N. Kambe, Pure Appl. Chem., 2010, 82, 565.
M. Toyofuku, S.-ichi Fujiwara, T. Shin-ike, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc., 2008, 130, 10504.
V. A. Potapov, V. N. Elokhina, L. I. Larina, T. I. Yaroshenko, A. A. Tatarinova, S. V. Amosova, J. Organomet. Chem., 2009, 694, 3679.
V. A. Potapov, R. S. Ishigeev, M. V. Musalov, S. V. Zinchenko, Yu. A. Chuvashev, T. N. Borodina, S. V. Amosova, Russ. J. Org. Chem., 2018, 54, 1798.
A. S. Medvedeva, M. V. Andreev, L. P. Safronova, Russ. J. Org. Chem., 2010, 46, 1466.
M. V. Andreev, A. S. Medvedeva, L. I. Larina, M. M. Demina, Mendeleev Commun., 2017, 27, 175.
M. V. Andreev, L. P. Safronova, A. S. Medvedeva, Russ. J. Org. Chem., 2011, 47, 1797.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2134–2136, November, 2019.
Rights and permissions
About this article
Cite this article
Andreev, M.V., Potapov, V.A., Musalov, M.V. et al. Regio- and stereoselective reaction of sodium benzeneselenolate with 3-(trimethylsilyl)prop-2-ynamides. Russ Chem Bull 68, 2134–2136 (2019). https://doi.org/10.1007/s11172-019-2679-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-019-2679-9