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Synlett 2005(9): 1429-1432  
DOI: 10.1055/s-2005-868498
LETTER
© Georg Thieme Verlag Stuttgart · New York

The First Example of Catalytic Aziridination Mediated by Arsonium Ylides: Preparation of trans-Pentafluorophenyl-Containing Aziridines

Shifa Zhua, Yuanxi Liaoa, Shizheng Zhu*a,b
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 20032, P. R. China
b College of Chemical Environmental, South China Normal University, Guangzhou, 510631, P. R. China
Fax: +86(21)64166128; e-Mail: zhusz@mail.sioc.ac.cn;
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Publikationsverlauf

Received 25 February 2005
Publikationsdatum:
27. April 2005 (online)

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Abstract

Triphenylarsine catalyzes the formation of aziridines from tosyl imines and aromatic diazo compounds in a one-pot reaction. It is the first example of catalytic aziridination mediated by ­arsonium ylides. It gave aziridines in excellent diastereoselectivity with pentafluorophenyl diazomethane as the substrate. This catalytic reaction is complementary with the reaction mediated by sulfur ylides.

Key words

diazocompound - ylide - fluorine - aziridine - catalyze

    References

  • 1a van Santen RA. Kuipers HPC. Adv. Catal.  1987,  35:  265 
    Suche in Google Scholar
  • 1b Zwanenburg B. ten Holte P. In Stereoselective Heterocyclic Synthesis III   Vol. 216:  Metz P. Topics in Current Chemistry, Springer; Berlin: 2001.  p.93-124  
    Suche in Google Scholar
  • 2 Müller P. Fruit C. Chem. Rev.  2003,  103:  2905 
    CrossrefSuche in Google Scholar
  • 3 Aggarwal VK. Alonson E. Fang G. Ferrara M. Hynd G. Porcelloni M. Angew. Chem., Int. Ed. Engl.  1994,  33:  599 
    CrossrefSuche in Google Scholar
  • 4a Aggarwal VK. Patel M. Studley J. Chem. Commun.  2002,  1514 
  • (b) Tewari RS. Chaturvedi SC. Tetrahedron Lett.  1977,  43:  3843 
    Suche in Google Scholar
  • For reviews on arsonium ylides:
  • (c) Lloyd D. Gosney I. Ormiston RA. Chem. Soc. Rev.  1987,  16:  45 
    Suche in Google Scholar
  • (d) Huang Y. Sheng Y. Adv. Organomet. Chem.  1982,  20:  113 
    Suche in Google Scholar
  • (e) Johnson AW. Ylide Chemistry   Academic Press; New York: 1966. 
  • 5 Zhu SF. Liao YX. Zhu SZ. Org. Lett.  2004,  6:  377 
    CrossrefSuche in Google Scholar
  • 6 Dudman CC. Reese CB. Synthesis  1982,  419 
    Thieme Connect
  • 7a Ramachandran PV. In Asymmetric Fluoroorganic Chemistry: Synthesis Applications and Future Directions, ACS Symposium Series 746   American Chemical Society; Washington DC: 2000. 
  • 7b Ojima I. McCarthy JR. Welch JT. In Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639   American Chemical Society; Washington DC: 1996. 
  • 7c Kukhar’ VP. Soloshonok VA. In Fluorine-containing Amino Acids: Synthesis and Properties   Wiley; New York: 1995. 
  • 7d Welch JT. In Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456   American Chemical Society; Washington DC: 1991. 
  • 7e Welch JT. Eswarakrishnan S. In Fluorine in Bioorganic Chemistry   Wiley & Sons; New York: 1991. 
  • 8a Strehmel B. Sarker AM. Malpert JH. Strehmel V. Seifert H. Neckers DC. J. Am. Chem. Soc.  1999,  121:  1226 
    Suche in Google Scholar
  • 8b Brooke GM. Mawson SD. J. Fluorine Chem.  1990,  50:  111 
    Suche in Google Scholar
  • 8c Feast WJ. Lovenich PW. Puschmann H. Taliani C. Chem. Commun.  2001,  505 
  • 8d Yu L. Bao Z. Adv. Mater.  1994,  6:  156 
    Suche in Google Scholar
  • 8e Coates GW. Dunn AR. Henling LM. Ziller JW. Lobkovskey EB. Grubbs RH. J. Am. Chem. Soc.  1998,  120:  3641 
    Suche in Google Scholar
  • 8f Krebs FC. Jensen T. J. Fluorine Chem.  2003,  120:  77 
    Suche in Google Scholar