Aza-Morita-Baylis-Hillman reaction of activated 1,3-butadienes with aldimines

WCC 12

Kristen N. Clary,, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, AB t2n1n4, Canada
The Morita-Baylis Hillman (MBH) Reaction has been widely studied as a coupling method for constructing allylic alcohols or amines from aldehydes or imines and activated alkenes. Recently, our group demonstrated that the MBH reaction of 1-(p-toluenesulfonyl)-1,3-butadiene (2a) with various aldimines 1 and subsequent cyclization of adducts 3a via conjugate addition and double bond isomerization, afforded substituted piperidine rings 4a, which are the core structures of numerous alkaloids and synthetic drugs. The coupling reactions proceeded best in the presence of 3-hydroxyquinuclidine (HQD) in DMF, while cyclization of the E isomers of 3a occurred in DMF and water with potassium carbonate as the base. A novel extension of the Morita-Baylis-Hillman reaction to other diene systems containing electronwithdrawing groups will be described.


The Merck Index Women in Chemistry
2:30 PM-4:30 PM, Monday, August 18, 2008 Pennsylvania Convention Center -- Hall C, Poster

Women Chemists Committee

The 236th ACS National Meeting, Philadelphia, PA, August 17-21, 2008