Unexpected addition of methyl 3,3,3-trifluoropyruvate to 'push-pull' enamines having a methyl group at α-position

Synthesis

Volumn , Issue 15, 2004, Pages 2545-2549

  Volochnyuk, Dmitriy M ^a   Kostyuk, Aleksandr N ^a   Sibgatulin, Dmitriy A ^a   Petrenko, Aleksandr E ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

'Push pull' enamines; Ene reaction; Methyl 3,3,3 trifluoropyruvate; Nucleophilic addition

Indexed keywords

ADDITION REACTIONS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

ENAMINES; POLYFUNCTIONALIZATION; PYRUVATE;

AMINES;

CARBONYL DERIVATIVE; ENAMINE; METHYL 3,3,3 TRIFLUOROPYRUVATE; METHYL GROUP; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 7644240169     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831216     Document Type: Article

References (28)

1. (a) Prakash, G. K. S.; Yan, P.; Toeroek, B.; Olah, G. A. Synlett 2003, 527.
2. (b) Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
3. (c) Soloshonok, V. A.; Kukhar', V. P. J. Org. Chem. USSR (Engl. Transl.) 1990, 26, 358.
4. (d) Golubev, A. S.; Kolomiets, A. F.; Fokin, A. V. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1989, 38, 2180.
5. Dolensky, B.; Kvicala, J.; Paleta, O.; Cejka, J. Tetrahedron Lett. 1996, 37, 6939.
6. (a) Golubev, A. S.; Sergeeva, N. N.; Hennig, L.; Kolomiets, A. F.; Burger, K. Tetrahedron 2003, 59, 1389.
7. (b) Eilitz, U.; Böttcher, C.; Sieler, J.; Gockel, S.; Haas, A.; Burger, K. Tetrahedron 2001, 57, 3921.
8. (c) Logothetis, T. A.; Eilitz, U.; Killer, W.; Burger, K. Tetrahedron 1998, 54, 14023.
9. Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663.
10. (a) Dyachenko, V. I.; Kolomiets, A. F.; Fokin, A. V. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1988, 37, 2306.
11. (b) Dyachenko, V. I.; Kolomiets, A. F.; Fokin, A. V. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1987, 36, 2646.
12. (c) Zelenin, A. E.; Chkanikov, N. D.; Kolomiets, A. F.; Fokin, A. V. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1986, 35, 1895.
13. (d) Chkanikov, N. D.; Sviridov, V. D.; Zelenin, A. E.; Tyutin, V. Yu.; Kolomiets, A. F.; Fokin, A. V. Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.) 1992, 41, 1415.
14. Palecec, J.; Paleta, O. Synthesis 2004, 521.
15. Pazenok, S. V.; Soloshonok, V. A.; Yagupol'skii, L. M. Chem. Heterocycl. Compd. (Engl. Transl.) 1990, 26, 115.
16. (a) Kostyuk, A. N.; Svyaschenko, Y. V.; Volochnyuk, D. M.; Lysenko, N. V.; Tolmachev, A. A. Tetrahedron Lett. 2003, 44, 6487.
17. (b) Kostyuk, A. N.; Volochnyuk, D. M.; Lysenko, N. V.; Pinchuk, A. M.; Tolmachev, A. A. Abstracts of the International Symposium Devoted to the 100th Anniversary of Academician A. V. Kirsanov, 21 August 2002; Kyiv: Ukraine, 2002, 39.
18. Volochnyuk, D. M.; Kostyuk, A. N.; Sibgatulin, D. A.; Chernega, A. N.; Pinchuk, A. M.; Tolmachev, A. A. Tetrahedron 2004, 60, 2361.
19. Böhme, H.; Tränka, M. Leibigs Ann. Chem. 1985, 149.
20. Kang, G. J.; Chan, T. H. Can. J. Chem. 1985, 63, 3102.
21. Kucklander, U. In The Chemistry of Enamines; Rappoport, Z., Ed.; Wiley: Chichester, 1994, Chap. 10, 523.
22. Sviridov, V. D.; Chkanikov, N. D.; Galakhov, M. V.; Shklyaev, Yu. V.; Shklyaev, V. S.; Aleksandrov, B. B.; Gavrilov,M. S. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1990, 39, 1268.
23. For examples of ene-reaction using MeTFP see: (a) Soloshonok, V. A.; Rozhenko, A. B.; Butovich, I. A.; Kukhar', V. P. J. Org. Chem. USSR (Engl. Transl.) 1990, 26, 1771.
24. (b) See also: Soloshonok, V. A.; Khotkevich, A. B.; Krasutskii, P. A. J. Org. Chem. USSR (Engl. Transl.) 1991, 27, 641.
25. For an example of ene-reaction of enamine 3 with the hydrazone of hexafluoroacetone, see: Burger, K.; Hein, F. Leibigs Ann. Chem. 1982, 5, 853.
26. (a) Hickmott, P. W.; Sheppard, G. J. Chem. Soc. (C) 1971, 1358.
27. (b) Dedina, J.; Kuthan, J.; Palecek, J.; Schraml, J. Collect. Czech. Chem. Commun. 1975, 40, 3476.
28. Paleta, O.; Palesek, J.; Dolensky, B. J. Fluorine Chem. 2001, 111, 147.