PDF herunterladen
Synlett 2011(16): 2321-2324  
DOI: 10.1055/s-0030-1261217
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Thermal [2+2] Cycloaddition of CF3-Substituted Allenynes: Access to Novel Cyclobutene-Containing α-Amino Acids

Artur K. Mailyana, Ivan M. Krylova, Christian Bruneaub, Pierre H. Dixneufb, Sergey N. Osipov*a
a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russian Federation
Fax: +7(499)1355085; e-Mail: osipov@ineos.ac.ru;
b Institute Sciences Chimiques de Rennes, UMR 6226 CNRS-Universite de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
Weitere Informationen

Publikationsverlauf

Received 27 June 2011
Publikationsdatum:
08. September 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

An efficient approach for the preparation of novel CF3-substituted cyclic α-amino acid derivatives fused with cyclobutene ring has been developed. The method is based on intramolecular thermal [2+2] cycloaddition of amino acid containing allenynes with internal triple bond obtained by successive [2,3]-sigmatropic rearrangement of propargyl-containing nitrogen CF3-ylides and ­Sonogashira derivatization of the triple bond.

Key words

allenynes - Sonogashira coupling - [2+2] cycloaddition - cyclobutenes - amino acids

    References

  • 1a Dembitsky VM. J. Nat. Med.  2008,  62:  1 
    Google Scholar
  • 1b Sergeiko A. Poroikov VV. Lumir O. Hanu LO. Dembitsky VM. Open Med. Chem. J.  2008,  2:  26 
    Google Scholar
  • 1c Worek F. Kirchner T. Baecker M. Szinicz L. Arch. Toxicol.  1996,  70:  497 
    Google Scholar
  • 1d Komiotis D. Manta S. Tsoukala E. Tzioumaki N. Anti-Infect. Agents Med. Chem.  2008,  7:  219 
    Google Scholar
  • 1e Frebault F. Luparia M. Oliveira MT. Goddard R. Maulide N. Angew. Chem. Int. Ed.  2010,  49:  5672 
    Google Scholar
  • 2a Carbocyclic Four-Membered Ring Compounds, In Methods of Organic Chemistry (Houben-Weyl)   Vol. 17f:  de Meijere A. Thieme; Stuttgart: 1997. 
    Google Scholar
  • 2b For a review, see: Luparia M. Audisio D. Maulide N. Synlett  2011,  735 ; and references cited therein
    Google Scholar
  • 3a Brummond KM. Chen D. Org. Lett.  2005,  7:  3473 
    Google Scholar
  • 3b Ohno H. Mizutani T. Kadoh Y. Miyamura K. Tanaka T. Angew. Chem. Int. Ed.  2005,  44:  5113 
    Google Scholar
  • 3c Jiang X. Ma S. Tetrahedron  2007,  63:  7589 
    Google Scholar
  • 3d Alcaide B. Almendros P. Aragoncillo C. Gómez-Campillos G. Eur. J. Org. Chem.  2011,  364 
    Google Scholar
  • 3e Inagaki F. Kitagaki S. Mukai C. Synlett  2011,  594 
    Google Scholar
  • 3f Alcaide B. Almendros P. Aragoncillo C. Chem. Soc. Rev.  2010,  39:  783 
    Google Scholar
  • 3g Painter TO. Wang L. Majumder S. Xie X.-Q. Brummond KM. ACS Comb. Sci.  2011,  13:  166 
    Google Scholar
  • 4a For reviews, see: Yua S. Ma S. Chem. Commun.  2011,  47:  5384 
    Google Scholar
  • 4b Ohno H. Mizutani T. Kadoh Y. Aso A. Miyamura K. Fujii N. Tanaka T. J. Org. Chem.  2007,  72:  4378 
    Google Scholar
  • 5 Vorobyeva DV. Mailyan AK. Peregudov AS. Karimova NM. Vasilyeva TP. Bushmarinov IS. Bruneau C. Dixneuf PH. Osipov SN. Tetrahedron  2011,  67:  3524 
    CrossrefGoogle Scholar
  • For recent reviews, see:
  • 6a Smits R. Cadicamo CD. Burger K. Koksch B. Chem. Soc. Rev.  2008,  37:  1727 
    Google Scholar
  • 6b Brigaud T. Chaume G. Pytkowicz J. Huguenot F. Chim. Oggi  2007,  25:  8 
    Google Scholar
  • 6c Qiu X.-L. Meng W.-D. Qing F.-L. Tetrahedron  2004,  60:  6711 
    Google Scholar
  • 6d Zanda M. New J. Chem.  2004,  28:  1401 
    Google Scholar
  • 7a Osipov SN. Artyushin OI. Kolomiets AF. Bruneau C. Picquet M. Dixneuf PH. Eur. J. Org. Chem.  2001,  3891 
    Google Scholar
  • 7b Osipov SN. Dixneuf PH. Russ. J. Org. Chem.  2003,  39:  1211 
    Google Scholar
  • 7c Eckert M. Monnier F. Shchetnikov GT. Titanyuk ID. Osipov SN. Dérien S. Dixneuf PH. Org. Lett.  2005,  7:  3741 
    Google Scholar
  • 7d Shchetnikov GT. Osipov SN. Bruneau C. Dixneuf PH. Synlett  2008,  578 
    Google Scholar
  • 8 Siebert MR. Osbourn JM. Brummond KM. Tantillo DJ. J. Am. Chem. Soc.  2010,  132:  11952 
    CrossrefGoogle Scholar