Synlett 2004(6): 1120-1121  
DOI: 10.1055/s-2004-822909
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Diazabicyclo[2.2.2]octane - DABCO

Vembaiyan Kannan*
D-206, Discovery Laboratory, Organic-III Division, Indian ­Institute of Chemical Technology, Tarnaka, Hyderabad-500007, ­India
e-Mail: vkan06@yahoo.com;
Further Information

Publication History

Publication Date:
08 April 2004 (online)

Introduction

Diazabicyclo[2.2.2]octane, DABCO (I), is the most commonly used catalyst in the Baylis-Hillman reaction. [1] This important carbon-carbon bond forming reaction has received much attention in recent years because it provides multifunctional molecules with a newly created stereocenter, which are versatile building blocks in organic ­synthesis.

The generally accepted mechanism is illustrated in Scheme 1 for the DABCO-catalyzed Baylis-Hillman ­reaction of benzaldehyde with methyl acrylate.

Scheme 1 DABCO catalyzed Baylis-Hillman reaction

    References

  • For review see:
  • 1a Basavaiah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
  • 1b Ciganek E. The Morita-Baylis-Hillman Reaction, In Organic Reactions   Vol. 51:  Paquette LA. John Wiley & Sons; New York: 1997.  p.201-350  
  • 1c Langer P. Angew. Chem. Int. Ed.  2000,  39:  3049 
  • 1d Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
  • 2 Baylis AB, and Hillman MED. inventors; German Patent  2155113.  1972; 1972,34174q
  • 3 Drewes SE. Njamela OL. Emslie ND. Ramesar N. Field JS. Synth. Commun.  1993,  23:  2807 
  • 4 Oishi T. Oguri H. Hirama M. Tetrahedron: Asymmetry  1995,  6:  1241 
  • 5 Brzezinski LJ. Rafel S. Leahy JW. J. Am. Chem. Soc.  1997,  119:  4317 
  • 6 Radha Krishna P. Kannan V. Ilangovan A. Sharma GVM. Tetrahedron: Asymmetry  2001,  12:  829 
  • 7 Radha Krishna P. Raja Sekhar E. Kannan V. Tetrahedron Lett.  2003,  44:  4973 
  • 8 Radha Krishna P. Kannan V. Sharma GVM. Ramana Rao MHV. Synlett  2003,  888 
  • 9 Yu C. Liu B. Hu L. J. Org. Chem.  2001,  66:  5413 
  • 10 Yu C. Hu L. J. Org. Chem.  2002,  67:  219 
  • 11 Kaye PT. Nocanda XW. J. Chem. Soc., Perkin Trans. 1  2000,  1331 
  • 12 Kaye PT. Nocanda XW. J. Chem. Soc., Perkin Trans. 1  2002,  1318