A convenient route to trifluoromethyl-substituted cyclopropane derivatives

Synthesis

Volumn , Issue 11, 2008, Pages 1757-1760

  Mykhailiuk, Pavel K ^a,b   Afonin, Sergii ^b   Ulrich, Anne S ^b   Komarov, Igor V ^a  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Alkenes; Amino acids; Catalysts; Diazo compounds; Fluorine

Indexed keywords

AMINES; AMINO ACIDS; CATALYSIS; CATALYSTS; COMPLEXATION; HEALTH; HYDROCARBONS; OLEFINS; ORGANIC ACIDS; TELLURIUM COMPOUNDS;

(Z) ALKENES; DIASTEREOISOMERS; GRAM SCALE; METAL CATALYSTS; SINGLE STEP; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); TARGET COMPOUNDS; TRIFLUORO METHYL;

PROPANE;

7 (TRIFLUOROMETHYL) 2 OXABICYCLO[4.1.0]HEPTANE; 7 (TRIFLUOROMETHYL)BICYCLO[4.1.0]HEPTANE; ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORINE DERIVATIVE; HEPTANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOPROPANATION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 45249118082     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067041     Document Type: Article

References (31)

1. (a) Faust, R. Angew. Chem. Int. Ed. 2001, 40, 2251.
2. Donaldson, W. A. Tetrahedron 2001, 57, 8589.
3. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.
4. (a) Fluorine-Containing Amino Acids Synthesis and Properties; Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: New York, 1994.
5. (b) Wang, R.; Ksebati, M. B.; Corbett, T. H.; Kern, E. R.; Drach, J. C.; Zemlicka, J. J. Med. Chem. 2001, 44, 4019.
6. (c) Ruzza, P.; Siligardi, G.; Donella-Deana, A.; Calderan, A.; Hussain, R.; Rubini, C.; Cesaro, L.; Osier, A.; Guiotto, A.; Pinna, L. A.; Borin, G. J. Pept. Sci. 2006, 12, 462.
7. (a) Pustovit, Y. M.; Ogojko, P. I.; Nazaretian, V. P.; Faryateva, L. B. J. Fluorine Chem. 1994, 69, 225.
8. (b) Hell, Z.; Finta, Z.; Dmowski, W.; Faigl, F.; Pustovit, Y. M.; Töke, L.; Harmat, V. J. Fluorine Chem. 2000, 104, 297.
9. (a) Wang, Y.; Zhao, X.; Li, Y.; Lu, L. Tetrahedron Lett. 2004, 45, 7775.
10. (b) Jiang, B.; Zhang, F.; Xiong, W. A. Chem. Commun. 2003, 536.
11. (a) Katagiri, T.; Irie, M.; Uneyama, K. Tetrahedron: Asymmetry 1999, 10, 2583.
12. (b) Katagiri, T.; Yamaji, S.; Handa, M.; Irie, M.; Uneyama, K. Chem. Commun. 2001, 2054.
13. Lin, P.; Jiang, J. Tetrahedron 2000,56,3635; and references therein.
14. (a) Atherton, J. H.; Fields, R. J. Chem. Soc. C 1967, 1450.
15. Atherton, J. H.; Fields, R. J. Chem. Soc. C 1968, 1507.
16. (a) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
17. Wang, Y.; Zhu, S.; Zhu, G.; Huang, Q. Tetrahedron 2001, 57, 7337.
18. (c) Jiang, B.; Zhang, X.; Luo, Z. Org. Lett. 2002, 4, 2453.
19. (d) Müller, P.; Grass, S.; Shahi, S. P.; Bernardinelli, G. Tetrahedron 2004, 60, 4755.
20. (e) Ghanem, A.; Lacrampe, F.; Aboul-Enein, H.; Schurig, V. Monatsh. Chem. 2005, 136, 1205.
21. (f) Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625.
22. Le Maux, P.; Juillard, S.; Simonneaux, G. Synthesis 2006, 10, 1701.
23. (a) Fujimoto, Y.; Irreverre, F.; Karle, J. M.; Karle, I. L.; Witkop, B. J. Am. Chem. Soc. 1971, 93, 3471.
24. (b) Doering, W. E.; Roth, W. R. Tetrahedron 1963, 19, 715; and references therein.
25. Notably, Simonneaux and co-workers observed the stereoselective formation of only the trans-isomer 3a, while performing the trifluoromethyl-cyclopropanation of 3 over chiral metalloporphyrins (reference 9).
26. (a) Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 3300.
27. (b) Salomon, R. G.; Salomon, M. F.; Heyne, T. R. J. Org. Chem. 1975, 40, 756.
28. Mitchell, R. E. Phytochemistry 1985, 7, 1485.
29. (a) Kolar, A. J.; Olsen, R. K. Synthesis 1977, 457.
30. Wieland, T.; Ohnacker, G.; Ziegler, W. Chem. Ber. 1957, 90, 194.
31. Katagiri, T.; Irie, M.; Uneyama, K. Org. Lett. 2000, 2, 2423.