Abstract
The stereochemistry of two processes, viz., α-ferrocenylalkylation of indazole with optically active S-(+)-1-ferrocenylethanol and the thermal rearrangement of S-(+)-2-N-(ferrocenylethyl)indazole into S-(+)-1-N-(ferrocenylethyl)indazole, was studied. Both reactions proceed stereoselectively.
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U. Burckhardt, L. Hintermann, A. Schnyder, and A. Togni, Organometallics, 1995, 14, 5415.
V. N. Boev, L. V. Snegur, V. N. Babin, and Yu. S. Nekrasov, Usp. Khim., 1997, 66, 677 [Russ. Chem. Rev., 1997, 66, 613 (Engl. Transl.)].
J. Fang, Z. Jin, Z. Li, and W. Liu, J. Organomet. Chem., 2003, 674, 1.
R. P. Hanzlik, P. Soine, and W. N. Soine, J. Med. Chem., 1979, 16, 33.
L. V. Popova, V. N. Babin, Yu. A. Belousov, Yu. S. Nekrasov, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, O. B. Bychenko, P. M. Raevskii, N. M. Morozova, A. I. Ilyina, and K. G. Shitkov, Appl. Organomet. Chem., 1993, 7, 85.
G. W. Gokel and I. K. Ugi, Angew. Chem., Int. Ed., 1971, 10, 191.
(a) D. Armstrong, W. DeMond, and B. P. Czech, Anal. Chem., 1985, 57, 48; (b) L. V. Snegur, V. I. Boev, Yu. S. Nekrasov, M. M. Ilyin, V. A. Davankov, Z. A. Starikova, A. I. Yanovsky, A. F. Kolomiets, and V. N. Babin, J. Organomet. Chem., 1999, 580, 26; (c) A. A. Simenel, Yu. V. Kuzmenko, E. A. Morozova, M. M. Ilyin, I. F. Gun'ko, and L. V. Snegur, J. Organomet. Chem., 2003, 688, 138; (d) A. Harada, K. Saeki, and S. Takahashi, Carbohydr. Res., 1989, 192, 1.
V. V. Gumenyuk, Z. A. Starikova, Yu. S. Nekrasov, and V. N. Babin, Izv. Akad. Nauk, Ser. Khim., 2002, 1744 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1894].
D. Marquarding, H. Klusacek, G. W. Gokel, P. Hoffmann, and I. K. Ugi, J. Am. Chem. Soc., 1970, 92, 5389.
Comprehensive Heterocyclic Chemistry, Eds. A. R. Katritzky and Ch. W. Rees, Pergamon Press, New York, 1984, 5, 169.
J. K. Lindsay and C. R. Hauser, J. Org. Chem., 1957, 22, 906.
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Simenel, A.A., Kuzmenko, Y.V., Ilyin, M.M. et al. Synthesis and properties of optically active ferrocenylethylindazoles. Russian Chemical Bulletin 53, 939–941 (2004). https://doi.org/10.1023/B:RUCB.0000037868.08052.23
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DOI: https://doi.org/10.1023/B:RUCB.0000037868.08052.23