Download PDF
Synthesis 2011(6): 972-978  
DOI: 10.1055/s-0030-1258433
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cobalt(I) Catalysis in the Diastereoselective Two-Step Synthesis of Tricyclic Systems

Florian Erver, Gerhard Hilt*, Klaus Harms
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: Hilt@chemie.uni-marburg.de;
Further Information

Publication History

Received 27 January 2011
Publication Date:
10 February 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The diastereoselective two-step synthesis of heterotricyclic systems is accomplished by regioselective cobalt-catalysed [4+2]- and [4+2+2]-cycloaddition reactions generating cyclohexa-1,4-diene and cycloocta-1,3,6-triene derivatives, and a hetero-Diels­-Alder reaction. Thus, a set of selected cyclohexadienes and cyclooctatrienes were reacted with cyclic 1,3-diones and formaldehyde in a Knoevenagel-hetero-Diels-Alder multicomponent reaction to produce a variety of tricyclic products.

Key words

alkyne - catalysis - cobalt - cycloaddition - diene - multicomponent reaction - hetero-Diels-Alder reaction

    References

  • For recent reviews, see:
  • 1a Leboeuf D. Gandon V. Malacria M. In Handbook of Cyclization Reactions   Vol. 1:  Ma S. Wiley-VCH; Weinheim: 2009.  p.367 
    Google Scholar
  • 1b Galan BR. Rovis T. Angew. Chem. Int. Ed.  2009,  48:  2830 
    Google Scholar
  • 1c Omae I. Appl. Organomet. Chem.  2008,  22:  149 
    Google Scholar
  • 1d Hess W. Treutwein J. Hilt G. Synthesis  2008,  3537 
    Google Scholar
  • 1e Omae I. Appl. Organomet. Chem.  2007,  21:  318 
    Google Scholar
  • 1f Kotha S. Brahmachary E. Lahiri K. Eur. J. Org. Chem.  2005,  4741 
    Google Scholar
  • 1g Malacria M. Aubert C. Renaud JL. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations   Vol. 1:  Lautens M. Trost BM. Thieme; Stuttgart: 2001.  p.439 
    Google Scholar
  • 1h Saito S. Yamamoto Y. Chem. Rev.  2000,  100:  2901 
    Google Scholar
  • 2a Hilt G. Paul A. Harms K. J. Org. Chem.  2008,  73:  5187 
    Google Scholar
  • 2b Hilt G. Paul A. Hengst C. Synthesis  2009,  3305 
    Google Scholar
  • 2c Hilt G. Hess W. Harms K. Synthesis  2008,  75 
    Google Scholar
  • 2d Treutwein J. Hilt G. Angew. Chem. Int. Ed.  2008,  47:  6811 
    Google Scholar
  • 2e Hilt G. Janikowski J. Angew. Chem. Int. Ed.  2008,  47:  5243 
    Google Scholar
  • 2f

    For alternative cobalt-catalysed reactions involving cyclopentadienyl cobalt-type catalyst systems, see reference 1.

  • For the application of cyclic and acyclic 1,4-dienes as synthons for 1,3-dicarbonyl compounds, see:
  • 3a Kersten L. Roesner S. Hilt G. Org. Lett.  2010,  12:  4920 
    Google Scholar
  • 3b Hilt G. Arndt M. Weske DF. Synthesis  2010,  1321 
    Google Scholar
  • 3c Hilt G. Weske DF. Chem. Soc. Rev.  2009,  38:  3082 
    Google Scholar
  • 4a Danz M. Hilt G. Adv. Synth. Catal.  2011,  in press
    Google Scholar
  • 4b Auvinet A.-L. Harrity JPA. Hilt G. J. Org. Chem.  2010,  75:  3893 
    Google Scholar
  • 5a Hilt G. Janikowski J. Org. Lett.  2009,  11:  773 
    Google Scholar
  • 5b Hilt G. Danz M. Synthesis  2008,  2257 
    Google Scholar
  • 5c Mörschel P. Janikowski J. Hilt G. Frenking G. J. Am. Chem. Soc.  2008,  130:  8952 
    Google Scholar
  • 5d Hilt G. Janikowski J. Hess W. Angew. Chem. Int. Ed.  2006,  45:  5204 
    Google Scholar
  • 6 Koser S. Hoffmann HMR. Heterocycles  1994,  37:  661 
    CrossrefGoogle Scholar
7

The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 809255 (6a) and CCDC 809256 (6d). These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033, E-mail: deposit@ccdc.cam.ac.uk].