Abstract
L-α-Amino acids catalyze 1,3-dipolar cycloaddition of methyl α-benzylideneamino acids to electron-deficient olefins in different solvents at room temperature. L-α-Amino acids ensure stereoselective formation of the corresponding syn,syn-azomethine ylides. The subsequent reaction with an active dipolarophile is stereospecific; it occurs as endo-cycloaddition with low asymmetric induction (up to ee 12%.). 3,4-Substituted 5-arylprolines were obtained in preparative yields using L-pyroglutamic acid or L-proline as catalyst.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Mauger, A.B., J. Nat. Prod., 1996, vol. 59, p. 1205.
Burton, G., Ku, T.W., Carr, T.J., Kiesow, T., Sarisky, R.T., Lin-Goerke, J., Baker, A., Earnshaw, D.L., Hofmann, G.A., Keenan, R.M., and Dhanak, D., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 1553; Zubia, A., Mendoza, L., Vivanco, S., Aldaba, E., Carrascal, T., Lecea, B., Arrieta, A., Zimmerman, T., Vidal-Vanaclocha, F., and Cossio, F.P., Angew. Chem., Int. Ed., 2005, vol. 44, p. 2903; Fournie-Zaluski, M., Coric, P., Thery, V., Gonzalez, W., Meudal, H., Turcaud, S., Michel, J., and Roques, B.P., J. Med. Chem., 1996, vol. 39, p. 2594; Murphy, M.M., Schullek, J.R., Gordon, E.M., and Gallop, M.A., J. Am. Chem. Soc., 1995, vol. 117, p. 7029.
Grigg, R., Chem. Soc. Rev., 1987, vol. 16, p. 89.
Tsuge, O. and Kanemasa, S., Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed., San Diego: Academic, 1989, p. 231.
Kudryavtsev, K.V., Nukolova, N.V., Kokoreva, O.V., and Smolin, E.S., Russ. J. Org. Chem., 2006, vol. 42, p. 412.
Kudryavtsev, K.V., Tsentalovich, M.Yu., Yegorov, A.S., and Kolychev, E.L., J. Heterocycl. Chem., 2006, vol. 43, p. 1461.
Cabrera, S., Arrayas, R.G., and Carretero, J.C., J. Am. Chem. Soc., 2005, vol. 127, p. 16 394.
Oderaotoshi, Y., Cheng, W., Fujitomi, S., Kasano, Y., Minakata, S., and Komatsu, M., Org. Lett., 2003, vol. 5, p. 5043.
Husinec, S. and Savic, V., Tetrahedron: Asymmetry, 2005, vol. 16, p. 2047.
Najera, C. and Sansano, J.M., Angew. Chem., Int. Ed., 2005, vol. 44, p. 6272.
Tsuge, O., Kanemasa, S., Ohe, M., Yorozu, K., Takenaka, S., and Ueno, K., Bull. Chem. Soc. Jpn., 1987, vol. 60, p. 4067.
Grigg, R., Gunaratne, H.Q.N., and Sridharan, V., Tetrahedron, 1987, vol. 43, p. 5887.
Dogan, O., Koyuncu, H., Garner, P., Bulut, A., Youngs, W.J., and Panzner, M., Org. Lett., 2006, vol. 8, p. 4687.
Marigo, M. and Jorgensen, K.A., Chem. Commun., 2006, p. 2001; List, B., Chem. Commun., 2006, p. 819; Lelais, G. and MacMillan, D.W.C., Aldrichim. Acta, 2006, vol. 39, p. 79; Berkessel, A. and Groger, H., Asymmetric Organocatalysis, Weinheim: Wiley, 2005; Seayad, J. and List, B., Org. Biomol. Chem., 2005, vol. 3, p. 719; Dalko, P.I. and Moisan, L., Angew. Chem., Int. Ed., 2004, vol. 43, p. 5138; Acc. Chem. Res., 2004, vol. 37 (special issue on organocatalysis).
List, B., Tetrahedron, 2002, vol. 58, p. 5573.
Amornraksa, K., Grigg, R., Gunaratne, H.Q.N., Kemp, J., and Sridharan, V., J. Chem. Soc., Perkin Trans. 1, 1987, p. 2285.
Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1988, p. 143.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 1990, vol. 46, p. 467.
SHELXL-97, Program for the Refinement of Crystal Structures, Gottingen: Univ. of Gottingen, 1997.
Tsuge, O., Kanemasa, S., and Yoshioka, M., J. Org. Chem., 1988, vol. 53, p. 1384.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © K.V. Kudryavtsev, A.A. Zagulyaeva, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 3, pp. 384–393.
Rights and permissions
About this article
Cite this article
Kudryavtsev, K.V., Zagulyaeva, A.A. 1,3-dipolar cycloaddition of schriff bases and electron-deficient alkenes, catalyzed by α-Amino acids. Russ J Org Chem 44, 378–387 (2008). https://doi.org/10.1134/S1070428008030123
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428008030123