Synthesis and structure of diastereomeric trans-3,4-diamino-2,2,6,6-tetramethylpiperidine1-oxyl derivatives
- 17 Downloads
The reaction of 3,4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl with (1S)-(+)-camphor-10-sulfonyl chloride gives a mixture of diastereomeric 4-monosulfonylamino derivatives. The products of their acylation have been obtained. The 3,4-bis-[(1S)-camphor-10-sulfonylamino] derivative was synthesized and resolved to individual diastereomers. For one of them thetrans relationship of the 3- and 4-substituents and the absolute (3S,4R)-configuration were established by X-ray structural analysis.
Key wordstrans-3.4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl diastereomeric derivatives, resolution structure absolute configuration
Unable to display preview. Download preview PDF.
- 1.V. D. Sen',Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2094 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 1928].Google Scholar
- 2.A. T. Quintanilha and R. J. Mehlhorn,FEBS Lett, 1978,91, 104.Google Scholar
- 3.D. D. Perrin, B. Dempsey and E. P. Serjeant,pK a Prediction for Organic Acids and Bases, Champan and Hall, London, 1981, 30.Google Scholar
- 4.B. V. Rozynov, R. I. Zhdanov, O. S. Reshetova, N. G. Kapitanova, Z. L. Gordon, and E. G. Rozantsev,Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 1838 [Bull. Acad. Sci. USSR, Div.Chem.Sci.,1978,27, No. 8].Google Scholar
- 5.R. A. Alden, J. Krant, and T. G. Taylor,J. Am. Chem. Soc., 1968,90, 74.Google Scholar
- 6.A. B. Zolotoi, P. M. Lukin, S. V. Konovalikhin, M. Yu. Skvortsova, O. E. Nasakin, and L. O. Atovmyan,Khim. Geterotsykl. Soedin., 1991, 519 [Chem. Heterocycl. Comp., 1991 (Engl. Transl.)].Google Scholar
- 7.A. Albert and E. Serjeant,Ionization Constants of Acids and Bases, J. Wiley and Sons, New York, 1962, 179 p.Google Scholar