Diazabicyclo[2.2.2]octane - DABCO

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.  ; ,34174q
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• 12 Kaye PT. Nocanda XW. J. Chem. Soc., Perkin Trans. 1  2002,  1318