Abstract
The effect of the nature of the central metal atom in chiral salen type complexes on the stereodifferentiating capacity of these complexes as catalysts in phase transfer asymmetric alkylation of Schiff"s base derived from alanine isopropyl ester and benzaldehyde by benzyl bromide. The nature of the central metal atom in the complex has a pronounced influence on the stereochemistry of alkylation; copper(ii) complexes exhibit the highest activity combined with a high stereoselectivity.
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References
E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Comprehensive Asymmetric Catalysis, Springer-Ferlag, Berlin, 2000.
M. J. O'Donnell, W. D. Bennet, and S. Wu, J. Am. Chem. Soc., 1989, 111, 2353.
J. Casas, C. Nájera, J. Sansano, J. González, J. Saá, and M. Vega, Tetrahedron Asymmetry, 2001, 12, 699.
T. Abellán, R. Chinchilla, N. Galindo, C. Nájera, and J. Sansano, Eur. J. Org. Chem., 2000, 2689.
B. Lygo, J. Crosby, and J. A. Peterson, Tetrahedron Lett., 1999, 40, 1385.
B. Lygo, Tetrahedron Lett., 1999, 40, 1389.
E. J. Corey, F. Xu, and M. C. Noe, J. Am. Chem. Soc., 1997, 119, 12414.
M. Horikawa, J. Busch-Petersen, and E. J. Corey, Tetrahedron Lett., 1999, 40, 3843.
T. Ooi, M. Kameda, and K. Maruoka, J. Am. Chem. Soc., 1999, 121, 6519.
T. Ooi, M. Takeuchi, M. Kameda, and K. Maruoka, J. Am. Chem. Soc., 2000, 121, 5228.
Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Haratynyan, Š. Vyskočil, M. North, and H. Kagan, Angew. Chem., Int. Ed. Engl., 2001, 40, 1948.
Y. N. Belokon, M. North, V. S. Kublitski, N. S. Ikonnikov, P. E. Krasik, and V. I. Maleev, Tetrahedron Lett., 1999, 40, 6105.
Y. N. Belokon, M. North, T. D. Churkina, N. S. Ikonnikov, and V. I. Maleev, Tetrahedron, 2001, 57, 2491.
C. Girard and H. Kagan, Angew. Chem., Int. Ed. Engl., 1998, 37, 2923.
E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, and C. Zepp, J. Org. Chem., 1994, 59, 1939.
A. R. Amundsen, J. Whelan, and B. Bosnich, Inorg. Chem., 1979, 18, 206.
Y. N. Belokon, S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Khrustalev, V. S. Larichev, M. A. Moscalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, and L. V. Yashkina, J. Am. Chem. Soc., 1999, 121, 118.
Yu. N. Belokon', V. M. Belikov, M. M. Dolgaya, I. I. Kruman, S. B. Nikitina, and P. V. Petrovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1973, 1836 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1973, 22 (Engl. Transl.)].
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Belokon", Y.N., Petrosyan, A.A., Maleev, V.I. et al. Metal-dependent stereochemistry of C—C bond formation under the asymmetric phase transfer catalysis by chiral salen complexes. Russian Chemical Bulletin 51, 2086–2089 (2002). https://doi.org/10.1023/A:1021672212599
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DOI: https://doi.org/10.1023/A:1021672212599