Abstract
The methylation of the lithium derivatives of the (11S,4S) and (11S,4R) diastereomers of 4-methyl-1-(α-methylbenzyl)azetidin-2-one proceeds stereospecifically with the formation of only trans-(3S,4S)- and trans-(3R,4R)-dimethyl-1-[(S)-α-methylbenzyl] azetidin-2-one, respectively. The process is accompanied by epimerization at the asymmetric center of the N-α-methylbenzyl substituent.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Y. Liwshitz and A. Singerman, J. Chem. Soc., C, No. 13, 1200 (1966).
R. G. Kostyanovskii (Kostyanovsky), I. M. Gella, V. I. Markov, and Z. E. Samoilova (Samoylova), Tetrahedron, 30, 39 (1974).
E. Rogalska and C. Belzecki, J. Org. Chem., 49, 1397 (1984).
K.-D. Kampe, German Offen. No. 1,807,496; Chem. Abstr., 73, 45313c (1970).
M. Shibasaki, Y. Ishida, G. Iwasaki, and T. Iimori, J. Org. Chem., 52, 3488 (1987).
N. N. Romanova, V. A. Budylin, G. V. Grishina, V. M. Potapov, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 1, 134 (1985).
N. N. Romanova, V. A. Budylin, G. V. Grishina, V. M. Potapov, M. L. Demchuk, I. Yu. Sivkova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 5, 607 (1986).
A. B. Hamlet and T. Durst, Can. J. Chem., 61, 411 (1983).
H. H. Otto, R. Mayerhofer, and H. J. Bergmann, Annalen, No. 7, 1159 (1983).
K. D. Barrow and T. M. Spotswood, Tetrahedron Lett., No. 37, 3325 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 914–920, July, 1990.
Rights and permissions
About this article
Cite this article
Romanova, N.N., Tallo, T.G., Borisenko, A.A. et al. Stereochemistry of the methylation of the (11S,4S) and (11S,4R) diastereomers of 4-methyl-1-(α-methylbenzyl)azetidin-2-one. Chem Heterocycl Compd 26, 761–767 (1990). https://doi.org/10.1007/BF00509703
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00509703