Regio-, stereo-, and enantioselective reactions of carbon acids catalyzed by recoverable organic catalysts bearing ionic liquid moieties

Pure and Applied Chemistry

Volumn 81, Issue 11, 2009, Pages 2059-2068

  Zlotin, Sergey G ^a   Kryshtal, Galina V ^a   Zhdankina, Galina M ^a   Kucherenko, Alexander S ^a   Bogolyubov, Andrei V ^a   Siyutkin, Dmitriy E ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Aldol reactions; Carbon acids; Dichlorocyclopropanation reactions; Enantio selective reactions; Ionic liquids; Michael reactions; Phase transfer catalysts; Recoverable organocatalysts

Indexed keywords

EID: 73849085798     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-08-12-05     Document Type: Conference Paper

References (37)

1. V. D. Pokhodenko, V. V. Pavlischuk. Theor. Exp. Chem. 38, 69 (2002).
2. L. M. Kustov, I. P. Beletskaya. Rossijskij Khim. Zh. 48, 3 (2004).
3. T. Welton. Chem. Rev. 99, 2071 (1999).
4. P. Wasserscheid, T. Welton (Eds.). Ionic Lliquids in Synthesis, p. 363, Wiley-VCH, Weinheim (2003).
5. P. I. Dalko (Ed.). Enantioselective Organocatalysis, p. 536, Wiley-VCH, Weinheim (2007).
6. Y. Sasson, G. Rothenberg. In Handbook of Green Chemistry and Technology, J. Clark, D. Macquarrie (Eds.), p. 206, Blackwell Science, Oxford (2002).
7. Al. Shestopalov, L. Rodinovskaya, An. Shestopalov, S. Zlotin, V. Nesterov. Synlett 2309 (2003).
8. S. Mukherjee, J. W. Yang, S. Hoffman, B. List. Chem. Rev. 107, 5471 (2007).
9. M. Gruttadauria, F. Giacalone, R. Noto. Chem. Soc. Rev. 37, 1666 (2008).
10. (a) R. Hagiwara, Y. Ito. J. Fluorine Chem. 105, 221 (2000);
11. (b) S. Cadra-Broch, A. Berthod, D. W. Armstrong. Anal. Bioanal. Chem. 375, 191 (2003);
12. (c) P. Bonhôte, A. P. Dias, N. Papageorgiu, K. Kalyanasundaram, M. Grätzel. Inorg. Chem. 35, 1168 (1996).
13. rd ed., Verlag Chemie, Weinheim (1993);
14. (b) C. Wheeler, K. N. West, C. L. Liotta, C. A. Eckert. Chem. Commun. 887 (2001);
15. (c) G. V. Kryshtal, G. M. Zhdankina, E. P. Serebryakov. Russ. J. Org. Chem., Engl. Transl. 30, 777 (1994);
16. (d) R. Ballini, G. Bosica. Tetrahedron Lett. 37, 8027 (1996);
17. (e) F. Sirovsky, C. Reichardt, M. Gorokhova, S. Ruban, E. Stoikova. Tetrahedron 55, 6363 (1999);
18. (f) F. Sirovsky, M. Gorokhova, S. Ruban. J. Mol. Catal. A 197, 213 (2003);
19. (g) S. Jubia, A. Ginebreda. Synthesis 682 (1977).
20. Ger. Offen. DE 3320544, Chem. Abstr. 101, 7482 (1984).
21. Eur. Pat. Appl. EP 0194693, Chem. Abstr. 111, 5730 (1989).
22. Eur. Pat. Appl. EP 110397, Chem. Abstr. 102, 6974 (1985).
23. G. V. Kryshtal, G. M. Zhdankina, S. G. Zlotin. Eur. J. Org. Chem. 2822 (2005).
24. D. G. Diana, U. J. Salvador, E. S. Zalay, R. E. Johnson, J. C. Collins, D. Johnson, W. B. Hinshaw, R. R. Lorenz, W. N. Thielking, F. Pancic, J. Med. Chem. 20, 750 (1977).
25. S. G. Zlotin, A. V. Bogolyubov, G. V. Kryshtal, G. M. Zhdankina, M. I. Struchkova, V. A. Tartakovsky. Synthesis 3849 (2006).
26. S. G. Zlotin, G. V. Kryshtal, G. M. Zhdankina, A. V. Bogolyubov, S. G. Postikova, V. A. Tartakovsky. Russ. Chem. Bull., Int. Ed. 56, 1487 (2007).
27. (a) U.S. Pat. US 3,991,086, Chem. Abstr. 86, 105925j (1977);
28. (b) U.S. Pat. US 4,495,201, Chem. Abstr. 102, 172652e (1985).
29. G. V. Kryshtal, G. M. Zhdankina, S. G. Zlotin. Eur. J. Org. Chem. 1777 (2008).
30. (a) M. Makosza, I. Krylova. Tetrahedron 55, 6395 (1999);
31. (b) M. Makosza. In Phase-Transfer Catalysis: Mechanisms and Synthesis, M. E. Halpern (Ed.), ACS Symposium Series No. 659, p. 41, American Chemical Society, Washington, DC (1997);
32. (c) C. L. Liotta, J. Berkner, J. Wright, B. Fair. In Phase-Transfer Catalysis: Mechanisms and Synthesis, M. E. Halpern (Ed.), ACS Symposium Series No. 659, p. 29, American Chemical Society, Washington, DC (1997);
33. (d) S. S. Yufit, G. V. Kryshtal, I. A. Esikova. In Phase-Transfer Catalysis: Mechanisms and Synthesis, M. E. Halpern (Ed.), ACS Symposium Series No. 659, p. 52, American Chemical Society, Washington, DC (1997).
34. S. Kucherenko, M. I. Struchkova, S. G. Zlotin. Eur. J. Org. Chem. 2000 (2006).
35. D. E. Siyutkin, A. S. Kucherenko, M. I. Struchkova, S. G. Zlotin. Tetrahedron Lett. 49, 1212 (2008).
36. D. E. Siyutkin, A. S. Kucherenko, S. G. Zlotin. Tetrahedron 65, 1366 (2009).
37. L. J. Whalen, C.-H. Wong. Aldrichim. Acta 39, 63 (2006).