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