Synlett 2003(12): 1934-1936  
DOI: 10.1055/s-2003-41458
CLUSTER
© Georg Thieme Verlag Stuttgart · New York

Effect of the Michael Acceptor in the Asymmetric Intramolecular Stetter Reaction

Mark S. Kerr, Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA
Fax: +1(970)4911801; e-Mail: rovis@lamar.colostate.edu;
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Publikationsverlauf

Received 20 June 2003
Publikationsdatum:
19. September 2003 (online)

Abstract

The effect of different Michael acceptors was evaluated in the catalytic asymmetric intramolecular Stetter reaction. Utilizing a readily prepared chiral triazolium salt as a nucleophilic carbene precursor, the reactivity and selectivity of substrates containing different electron-deficient double bonds was shown to vary significantly under identical reaction conditions.

    References

  • 1 Seebach D. Angew. Chem., Int. Ed. Engl.  1979,  18:  239 
  • 2 Stetter H. Kuhlmann H. Organic Reactions   Vol. 40:  Paquette LA. Wiley; New York: 1991.  p.407 
  • 3 Stetter H. Kuhlmann H. Chem. Ber.  1976,  109:  2891 
  • 4 Stetter H. Kuhlmann H. Chem. Ber.  1976,  109:  3427 
  • 5 Ciganek E. Synthesis  1995,  1311 
  • 6 Enders D. Breuer K. Runsink J. Teles JH. Helv. Chim. Acta  1996,  79:  1899 
  • The mechanistically related asymmetric benzoin reaction has received far more attention, see:
  • 7a Sheehan JC. Hunneman DH. J. Am. Chem. Soc.  1966,  88:  3666 
  • 7b Sheehan JC. Hara T. J. Org. Chem.  1974,  39:  1196 
  • 7c Martí J. Castells J. López-Calahorra F. Tetrahedron Lett.  1993,  34:  521 
  • 7d Yamashita K. Sasaki S.-i. Osaki T. Nango M. Tsuda K. Tetrahedron Lett.  1995,  36:  4817 
  • 7e Enders D. Breuer K. Teles JH. Helv. Chim. Acta  1996,  79:  1217 
  • 7f Knight RL. Leeper FJ. Tetrahedron Lett.  1997,  38:  3611 
  • 7g Gerhard AU. Leeper FJ. Tetrahedron Lett.  1997,  38:  3615 
  • 7h Dvorak CA. Rawal VH. Tetrahedron Lett.  1998,  39:  2925 
  • 7i Knight RL. Leeper FJ. J. Chem. Soc., Perkin Trans. 1  1998,  1891 
  • 7j Enders D. Kallfass U. Angew. Chem. Int. Ed.  2002,  41:  1743 
  • 8 Kerr MS. Read de Alaniz J. Rovis T. J. Am. Chem. Soc.  2002,  124:  10298 
  • 9 Enders D. Breuer K. Raabe G. Runsink J. Teles JH. Melder J.-P. Ebel K. Brode S. Angew Chem., Int. Ed. Engl.  1995,  34:  1021 
  • 10a Alder RW. Allen PR. Williams S. J. Chem. Commun.  1995,  1267 
  • 10b Kim Y.-J. Streitwieser A. J. Am. Chem. Soc.  2002,  124:  5757