Boron-catalyzed direct aldol reactions of pyruvic acids


Doris Lee,, Corey A. McClary, Stephen G. Newman, and Mark S. Taylor, Department of Chemistry, University of Toronto, Lash Miller Chemical Laboratories, 80 St. George Street, Toronto, ON M5S 3H6, Canada
The direct aldol reaction, in which a catalytic amount of an enolate is generated in situ, is a powerful tool in the generation of carbon-carbon bonds. While catalytic methods employing metals and amine-based catalysts have been extensively studied, aldol reactions employing stoichiometric amounts of boron continue to be used in total synthesis. We have developed the first boron-catalyzed direct aldol reaction of pyruvic acids with aldehydes towards the synthesis of isotetronic acids. These types of products are pharmaceutically significant as they can be used as building blocks for complex unnatural sugars. There is great potential for this methodology in that asymmetric isotetronic acids may be generated using substoichiometric quantities of a chiral boron reagent.


The Merck Index Women in Chemistry
2:30 PM-4:30 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Poster

Women Chemists Committee

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009