Abstract
A method for the highly enantioselective synthesis of (3S)- and (3R)-3,3-disubstituted 4-piperidones with an optical purity of 98% based on the “deracemizing” alkylation of 3-substituted 4-piperidones during Michael addition of their chiral imines to electrophilic alkenes was developed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. F. Martin, Tetrahedron, 36, 419 (1980).
D. Enders, K. Papadopoulos, B. E. M. Rendenbach, R. Appel, and F. Knock, Tetrahedron Lett., 27, 3491 (1986).
K. Tomioka, K. Ando, K. Yasuda, and K. Koga, Tetrahedron Lett., 27, 715 (1986).
B. Nebout, B. de Jeso, and J.-C. Pommier, J. Chem. Soc., Chem. Commun., No. 8, 504 (1985).
M. Pfau, G. Revial, A. Guingant, and J. d'Angelo, J. Am. Chem. Soc., 107, 273 (1985).
G. V. Grishina, S. A. Abdulganeeva, V. M. Potapov, I. A. Ivanova, A. A. Espenbetov, Yu. T. Struchkov, I. A. Grishina, and A. I. Lutsenko, Khim. Geterotsikl. Soedin., No. 12, 1656 (1985).
T. Volpe, G. Revial, and J. d'Angelo, Tetrahedron Lett., 28, 2367 (1987).
Y. Hirai, T. Terada, and T. Yamazaki, J. Am. Chem. Soc., 110, 958 (1988).
A. Sevin, J. Tortajada, and M. Pfau, J. Org. Chem., 51, 2671 (1986).
D. R. Howton, J. Org. Chem., 10, 277 (1945).
V. V. Dunina, E. G. Rukhadze, and V. M. Potapov, Production and Investigation of Optically Active Substances [in Russian], Izd. Moskovsk. Gosudarstv. Univ., Moscow (1979), p. 292.
O. Yu. Magidson, Zh. Obshch. Khim., 11, 339 (1941).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1072–1078, August, 1992.
Rights and permissions
About this article
Cite this article
Grishina, G.V., Gaidarova, E.L. Highly enantioselective synthesis of 3,3-disubstituted 4-piperidones by michael alkylation of chiral piperidone imines. Chem Heterocycl Compd 28, 898–904 (1992). https://doi.org/10.1007/BF00531322
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00531322