Download PDF
Synthesis 2007(3): 442-446  
DOI: 10.1055/s-2007-965882
PAPER
© Georg Thieme Verlag Stuttgart · New York

Pauson-Khand Carbonylative Cocyclizations of Acetylenes with Cyclopropylallenes [1]

Mohammed Ahmara, Mario Knokeb, Armin de Meijere*b, Bernard Cazes*a
a Université Claude Bernard-LYON, UMR-CNRS 5181, Laboratoire de Chimie Organique 1, Bât. CPE-Lyon, 43 Bd. du 11 Novembre 1918, 69622 Villeurbanne, France
Fax: +33(4)72431214; e-Mail: cazes@univ-lyon1.fr;
b Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399472; e-Mail: ameijer1@gwdg.de;
Further Information

Publication History

Received 14 July 2006
Publication Date:
12 January 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

The Pauson-Khand-like carbonylative cocyclizations of alkynes with cyclopropylallene and with 1,3-dicyclopropylallene occur regioselectively and lead to 4-(cyclopropylmethylene)cyclopentenones (43-59% for six examples).

Key words

cobalt complexes - cycloaddition - cyclopropylallenes - cyclopentenones - small rings

    References

  • For AdM, this is to count as Part 137 in the series ‘Cyclopropyl Building Blocks for Organic Synthesis’.
  • 1a For Part 136, see: Osipova A. Yufit DS. de Meijere A. Synthesis  2006,  131 
    CrossrefGoogle Scholar
  • 1b For Part 134, see: von Seebach M. Kozhushkov SI. Frank D. Boese R. Benet-Buchholz J. Yufit DS. Schill H. de Meijere A. Chem. Eur. J.  2007,  13:  167 
    CrossrefGoogle Scholar
  • 2 Khand IU. Knox GR. Pauson PL. Watts WE. Foreman MI. J. Chem. Soc., Perkin Trans. 1  1973,  977 
    CrossrefGoogle Scholar
  • For recent reviews, see:
  • 3a Laschat S. Becheanu A. Bell T. Baro A. Synlett  2005,  2547 
    Google Scholar
  • 3b Park KH. Chung YK. Synlett  2005,  545 
    Google Scholar
  • 3c Rodríguez Rivero M. Adrio J. Carretero JC. Synlett  2005,  26 
    Google Scholar
  • 3d Gibson SE. Mainolfi N. Angew. Chem. Int. Ed.  2005,  44:  3022 
    Google Scholar
  • 3e Bonaga LVR. Krafft ME. Tetrahedron  2004,  60:  9795 
    Google Scholar
  • 3f Sugihara T. Yamagushi M. Nishizawa M. Chem. Eur. J.  2001,  7:  1589 
    Google Scholar
  • 3g Brummond KM. Kent JL. Tetrahedron  2000,  56:  3263 
    Google Scholar
  • 3h Chung YK. Coord. Chem. Rev.  1999,  188:  297 
    Google Scholar
  • 3i Schore NE. Comprehensive Organometallic Chemistry II   Vol. 12:  Abel EW. Stone FGA. Wilkinson G. Elsevier; New York: 1995.  p.703-739  
    Google Scholar
  • For recent applications, see:
  • 4a Krafft ME. Cheung YY. Abboud KA. J. Org. Chem.  2001,  66:  7443 
    CrossrefGoogle Scholar
  • 4b Kerr WJ. McLaughlin M. Morrison AJ. Pauson PL. Org. Lett.  2001,  3:  2945 
    CrossrefGoogle Scholar
  • 4c Nomura I. Mukai C. Org. Lett.  2002,  4:  4301 
    CrossrefGoogle Scholar
  • 4d Ishizaki M. Niimi Y. Hoshino O. Tetrahedron Lett.  2003,  44:  6029 
    CrossrefGoogle Scholar
  • 5a Ahmar M. Antras F. Cazes B. Tetrahedron Lett.  1995,  36:  4417 
    CrossrefGoogle Scholar
  • 5b Antras F. Ahmar M. Cazes B. Tetrahedron Lett.  2001,  42:  8153 
    CrossrefGoogle Scholar
  • 5c Antras F. Ahmar M. Cazes B. Tetrahedron Lett.  2001,  42:  8157 
    CrossrefGoogle Scholar
  • 6 Ahmar M. Locatelli C. Colombier D. Cazes B. Tetrahedron Lett.  1997,  38:  5281 
    Google Scholar
  • 7a For a review on intramolecular PKR’s of allenynes, see: Brummond KM. In Advances in Cycloadditions   Vol. 6:  Harmata M. JAI Press Inc; Stamford, CT: 1999.  p.211 
    Google Scholar
  • 7b Brummond KM. Curran DP. Mitasev B. Fischer S. J. Org. Chem.  2005,  70:  1745 ; and references cited therein
    Google Scholar
  • 8 Ahmar M. Chabanis O. Gauthier J. Cazes B. Tetrahedron Lett.  1997,  38:  5277 
    Google Scholar
  • 9 For a recent review, see: Sydnes LK. Chem. Rev.  2003,  103:  1133 
    CrossrefPubMedGoogle Scholar
  • 10a Murakami M. Itami K. Ubukata M. Tsuji I. Ito Y. J. Org. Chem.  1998,  63:  4 
    CrossrefGoogle Scholar
  • 10b Hayashi M. Ohmatsu T. Meng Y.-P. Saigo K. Angew. Chem. Int. Ed.  1998,  37:  837 
    CrossrefGoogle Scholar
  • 10c Knoke M. de Meijere A. Synlett  2003,  195 
    CrossrefGoogle Scholar
  • 10d Knoke M. de Meijere A. Eur. J. Org. Chem.  2005,  2259 
    CrossrefGoogle Scholar
  • 11a Stolle A. Becker H. Salaün J. de Meijere A. Tetrahedron Lett.  1994,  35:  3517 
    CrossrefGoogle Scholar
  • 11b Stolle A. Becker H. Salaün J. de Meijere A. Tetrahedron Lett.  1994,  35:  3521 
    CrossrefGoogle Scholar
  • 11c de Meijere A. Becker H. Stolle A. Kozhushkov SI. Bes MT. Salaün J. Noltemeyer M. Chem. Eur. J.  2005,  11:  2471 
    CrossrefGoogle Scholar
  • 11d Kurahashi T. de Meijere A. Angew. Chem. Int. Ed.  2005,  44:  7881 
    CrossrefGoogle Scholar
  • 12a Iwasawa N. Owada Y. Matsuo T. Chem. Lett.  1995,  115 
    CrossrefGoogle Scholar
  • 12b Owada Y. Matsuo T. Iwasawa N. Tetrahedron  1997,  53:  11069 
    CrossrefGoogle Scholar
  • 13 Baldwin JE. Chem. Rev.  2003,  103:  1197 
    CrossrefPubMedGoogle Scholar
  • 14a Greenfield H. Wender I. Wotiz JH. J. Org. Chem.  1956,  21:  875 
    CrossrefGoogle Scholar
  • 14b Sovago J. Newton MG. Mushina EA. Ungvary F. J. Am. Chem. Soc.  1996,  118:  9589 
    CrossrefGoogle Scholar
  • 15 Searles S. Li Y. Nassim B. Lopes M.-TR. Tran PT. Crabbé P. J. Chem. Soc., Perkin Trans. 1  1984,  747 
    CrossrefGoogle Scholar
  • 16 Dicyclopropylacetylene was prepared from commercially available cyclopropylacetylene and 1-bromo-3-chloropropane via 5-chloro-1-cyclopropylpent-1-yne, adopting a published procedure for the conversion of 1,8-dichlorooct-4-yne to dicyclopropylacetylene: Militzer H.-C. Schömenauer S. Otte C. Puls C. Hain J. Bräse S. de Meijere A. Synthesis  1993,  998 
    Article in Thieme ConnectGoogle Scholar
  • 17 Roth WR. Schmidt T. Humbert H. Chem. Ber.  1975,  108:  2171 
    CrossrefGoogle Scholar