Synthesis 2008(11): 1757-1760  
DOI: 10.1055/s-2008-1067041
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Route to Trifluoromethyl-Substituted Cyclopropane Derivatives

Pavel K. Mykhailiuka,c, Sergii Afoninb, Anne S. Ulrichb,c, Igor V. Komarov*a
a Kyiv National Taras Shevchenko University, 01033 Kyiv, Ukraine
e-Mail: ik214@yahoo.com;
b Institute of Biological Interfaces, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
c Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
Further Information

Publication History

Received 11 December 2007
Publication Date:
29 April 2008 (eFirst)

Abstract

A range of alkenes have been converted in a single step into the corresponding trifluoromethyl-substituted cyclopropanes by treatment with 2-diazo-l,l,l-trifluoroethane over metal catalysts. Application of the Gaspar-Roth procedure allowed the preparation of target compounds on a multi-gram scale. The practical utility of this reaction has been demonstrated by the synthesis of both diastereoisomers of the non-natural amino acid trifluoronorcoronamic acid in two steps.

    References

  • 1a Faust R. Angew. Chem. Int. Ed.  2001,  40:  2251 
  • 1b Donaldson WA. Tetrahedron  2001,  57:  8589 
  • 1c Wessjohann LA. Brandt W. Thiemann T. Chem. Rev.  2003,  103:  1625 
  • 2a Fluorine-Containing Amino Acids Synthesis and Properties   Kukhar VP. Soloshonok VA. John Wiley & Sons; New York: 1994. 
  • 2b Wang R. Ksebati MB. Corbett TH. Kern ER. Drach JC. Zemlicka J. J. Med. Chem.  2001,  44:  4019 
  • 2c Ruzza P. Siligardi G. Donella-Deana A. Calderan A. Hussain R. Rubini C. Cesaro L. Osler A. Guiotto A. Pinna LA. Borin G. J. Pept. Sci.  2006,  12:  462 
  • 3a Pustovit YM. Ogojko PI. Nazaretian VP. Faryateva LB. J. Fluorine Chem.  1994,  69:  225 
  • 3b Hell Z. Finta Z. Dmowski W. Faigl F. Pustovit YM. Töke L. Harmat V. J. Fluorine Chem.  2000,  104:  297 
  • 4a Wang Y. Zhao X. Li Y. Lu L. Tetrahedron Lett.  2004,  45:  7775 
  • 4b Jiang B. Zhang F. Xiong WA. Chem. Commun.  2003,  536 
  • 5a Katagiri T. Irie M. Uneyama K. Tetrahedron: Asymmetry  1999,  10:  2583 
  • 5b Katagiri T. Yamaji S. Handa M. Irie M. Uneyama K. Chem. Commun.  2001,  2054 
  • 6 Lin P. Jiang J. Tetrahedron  2000,  56:  3635 ; and references therein
  • 7a Atherton JH. Fields R. J. Chem. Soc. C  1967,  1450 
  • 7b Atherton JH. Fields R. J. Chem. Soc. C  1968,  1507 
  • 8a Adams J. Spero DM. Tetrahedron  1991,  47:  1765 
  • 8b Wang Y. Zhu S. Zhu G. Huang Q. Tetrahedron  2001,  57:  7337 
  • 8c Jiang B. Zhang X. Luo Z. Org. Lett.  2002,  4:  2453 
  • 8d Müller P. Grass S. Shahi SP. Bernardinelli G. Tetrahedron  2004,  60:  4755 
  • 8e Ghanem A. Lacrampe F. Aboul-Enein H. Schurig V. Monatsh. Chem.  2005,  136:  1205 
  • 8f Denton JR. Sukumaran D. Davies HML. Org. Lett.  2007,  9:  2625 
  • 9 Le Maux P. Juillard S. Simonneaux G. Synthesis  2006,  10:  1701 
  • 10a Fujimoto Y. Irreverre F. Karle JM. Karle IL. Witkop B. J. Am. Chem. Soc.  1971,  93:  3471 
  • 10b Doering WE. Roth WR. Tetrahedron  1963,  19:  715 ; and references therein
  • 12a Salomon RG. Kochi JK. J. Am. Chem. Soc.  1973,  95:  3300 
  • 12b Salomon RG. Salomon MF. Heyne TR. J. Org. Chem.  1975,  40:  756 
  • 13 Mitchell RE. Phytochemistry  1985,  7:  1485 
  • 14a Kolar AJ. Olsen RK. Synthesis  1977,  457 
  • 14b Wieland T. Ohnacker G. Ziegler W. Chem. Ber.  1957,  90:  194 
  • 15 Katagiri T. Irie M. Uneyama K. Org. Lett.  2000,  2:  2423 
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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).