An investigation of the formation of enol acrylates from the acid-catalyzed reactions of various ketones with ethyl diazoacetate

ORGN 591

Bryan Branstetter and M. Mahmun Hossain. University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53211
Our group has discovered that HBF4•OEt2 can catalyze the reaction between aromatic aldehydes and ethyl diazoacetate to produce β-hydroxy acrylates and β-keto esters in good yields. To further advance this idea we shifted our attention to the more unreactive aromatic, cyclic, and aliphatic ketones, to investigate if they to will produce the desired β-hydroxy acrylates in good yield. Our group is currently interested in acrylates because we feel they have potential for further downstream synthesis of important biologically active compounds.