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
Preview

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 
    Search in Google Scholar
  • 1b Galan BR. Rovis T. Angew. Chem. Int. Ed.  2009,  48:  2830 
    Search in Google Scholar
  • 1c Omae I. Appl. Organomet. Chem.  2008,  22:  149 
    Search in Google Scholar
  • 1d Hess W. Treutwein J. Hilt G. Synthesis  2008,  3537 
  • 1e Omae I. Appl. Organomet. Chem.  2007,  21:  318 
    Search in Google Scholar
  • 1f Kotha S. Brahmachary E. Lahiri K. Eur. J. Org. Chem.  2005,  4741 
  • 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 
    Search in Google Scholar
  • 1h Saito S. Yamamoto Y. Chem. Rev.  2000,  100:  2901 
    Search in Google Scholar
  • 2a Hilt G. Paul A. Harms K. J. Org. Chem.  2008,  73:  5187 
    Search in Google Scholar
  • 2b Hilt G. Paul A. Hengst C. Synthesis  2009,  3305 
  • 2c Hilt G. Hess W. Harms K. Synthesis  2008,  75 
  • 2d Treutwein J. Hilt G. Angew. Chem. Int. Ed.  2008,  47:  6811 
    Search in Google Scholar
  • 2e Hilt G. Janikowski J. Angew. Chem. Int. Ed.  2008,  47:  5243 
    Search in 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 
    Search in Google Scholar
  • 3b Hilt G. Arndt M. Weske DF. Synthesis  2010,  1321 
  • 3c Hilt G. Weske DF. Chem. Soc. Rev.  2009,  38:  3082 
    Search in Google Scholar
  • 4a Danz M. Hilt G. Adv. Synth. Catal.  2011,  in press
  • 4b Auvinet A.-L. Harrity JPA. Hilt G. J. Org. Chem.  2010,  75:  3893 
    Search in Google Scholar
  • 5a Hilt G. Janikowski J. Org. Lett.  2009,  11:  773 
    Search in Google Scholar
  • 5b Hilt G. Danz M. Synthesis  2008,  2257 
  • 5c Mörschel P. Janikowski J. Hilt G. Frenking G. J. Am. Chem. Soc.  2008,  130:  8952 
    Search in Google Scholar
  • 5d Hilt G. Janikowski J. Hess W. Angew. Chem. Int. Ed.  2006,  45:  5204 
    Search in Google Scholar
  • 6 Koser S. Hoffmann HMR. Heterocycles  1994,  37:  661 
    CrossrefSearch in Google 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].