Abstract
The methylation of the lithium derivative of azethidinone-2 which has a chiral substituent at the nitrogen atom is asymmetrical and leads, with an optical yield of 35%, to diastereomeric 3-methylated azethidinones-2. The reaction of these compounds with Na in liquid ammonia gives enantiomeric 3-methylazethidinones which confirms that an asymmetrical synthesis has taken place.
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V. M. Giriyavallabhan, A. K. Ganguly, S. W. McCombi, P. Pinto and R. Rizvy, Tetrahedron Lett., No. 36, 3485 (1981).
C. M. Cimarusti, H. E. Applegate, H. W. Chang, D. M. Floyd, W. H. Koster, W. A. Slusarchyk, and M. G. Young, J. Org. Chem., 47, 179 (1982).
T. Durst and M. J. LeBelle, Canad. J. Chem., 50, 3196 (1972).
H. Otto and R. Mayrhofer, Ann., 7, 1152 (1983).
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, V. N. Torochesnikov, M. L. Demchuk, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 12, 1644 (1984).
S. T. Hodgson, D. M. Hollinshead, and S. V. Ley, Chem. Comm., No. 8, 494 (1984).
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Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 607–611, May, 1986.
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Romanova, N.N., Budylin, V.A., Grishina, G.V. et al. Asymmetrical alkylation of 1-[(s)-α-phenylethyl]-azethidinone-2. Chem Heterocycl Compd 22, 495–499 (1986). https://doi.org/10.1007/BF00519526
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DOI: https://doi.org/10.1007/BF00519526