Abstract
An efficient one-pot method was developed for the synthesis of 3-alkyland 3-benzyl-substituted phospholanes through the successive Cp2ZrCl2-catalyzed cycloalumination of α-olefins in the presence of AlEt3 giving the corresponding aluminacyclopentanes followed by the in situ replacement of the aluminum atom in the latter compounds by a P atom by means of methyl(phenyl)dichlorophosphines. The oxidation of 3-alkyl- and 3-benzyl-1-methyl(phenyl)-phospholanes with hydrogen peroxide affords 3-alkyl- and 3-benzyl-1-methyl(phenyl)-phospholane 1-oxides, respectively.
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V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, T. V. Tyumkina, U. M. Dzhemilev, Russ. Chem. Bull. (Int. Ed.), 2012, 61, No. 1 [Izv. Akad. Nauk, Ser. Khim., 2012, 156].
G. Keglevich, H. Forintos, G. M. Keseru, L. Hegedüs, L. Tőke, Tetrahedron, 2000, 56, 4823.
M. Yamashita, V. K. Reddy, L. N. Rao, B. Haritha, M. Maeda, K. Suzuki, H. Totsuka, M. Takahashi, T. Oshikawa, Tetrahedron Lett., 2003, 44, 2339.
L. Kollar, G. Keglevich, Chem. Rev., 2010, 110, 4257.
B. Breit, E. Fuchs, Chem. Commun., 2004, 694.
J. Klosin, C. R. Landis, Acc. Chem. Ress., 2007, 40, 1251.
M. Yamada, M. Yamashita, T. Suyama, J. Yamashita, K. Asai, T. Niimi, N. Ozaki, M. Fujie, K. Maddali, S. Nakamura, K. Ohnishi, Bioorg. Med. Chem. Lett., 2010, 20, 5943.
L. D. Quin, The Heterocyclic Chemistry of Phosphorus: Systems Based on the Phosphorus-Carbon Bond, Wiley-Interscience, New York, 1981, p. 500.
G. Markl, Angew. Chem. Int. Ed., 1965, 12, 1023.
Y. Zhou, X. Yan, C. Xi, Tetrahedron Lett., 2010, 51, 6136.
P. J. Fagan, W. A. Nugent, J. C. Calabrese, J. Am. Chem. Soc., 1994, 116, 1880.
U. M. Dzhemilev, Mendeleev Commun., 2008, 18, 1.
U. M. Dzhemilev, A. G. Ibragimov, Usp. Khim., 2000, 69, 134 [Russ. Chem. Rev. (Engl. Transl.), 2000, 69)].
V. M. Potapov, Stereokhimiya [Stereochemistry], Khimiya, Moscow, 1988, 464 pp. (in Russian).
O. Kühl, Phosphorus-31 NMR Spectroscopy: a Concise Introduction for the Synthetic Organic and Organometallic Chemist, Springer, Berlin, 2008, p. 131.
D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.
R. Kh. Freidlina, E. M. Brainina, A. N. Nesmeyanov, Dokl. Akad. Nauk SSSR, 1969, 138, 1369 [Dokl. Chem. (Engl. Transl.), 1969].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1540–1543, August, 2012.
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D’yakonov, V.A., Makhamatkhanova, A.L., Tyumkina, T.V. et al. Synthesis and transformations of metallacycles 40. Catalytic cycloalumination in the synthesis of 3-substituted phospholanes. Russ Chem Bull 61, 1556–1559 (2012). https://doi.org/10.1007/s11172-012-0205-4
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DOI: https://doi.org/10.1007/s11172-012-0205-4