W. Peng, Jingwei Zhao, Shizheng Zhu
Mar 1, 2006
Citations
0
Influential Citations
6
Citations
Journal
ChemInform
Abstract
Abstract Synthetic applications of ethyl 3-bromodifluoromethyl-3-benzyloxy-acrylate as a versatile and multifunctionalized gem -difluorination building block to introduce difluoromethene subunit into some new hydroxy esters have been investigated. It was found that its zinc mediated reaction with a variety of aldehyde in DMF gave the Reformatsky reaction mode product, β-hydroxy ester, in good yield, while its tetrakis(dimethylamino)ethylene (TDAE) promoted reaction with a limited scope of aldehyde produced Barbier reaction mode product, δ-hydroxy ester, in moderate yield. The reaction of its zinc reagent with styrene oxide resulted in rearrangement of the epoxide to 2-phenyl-acetaldehyde, and then the zinc reagent condensed with this aldehyde to provide the Reformastsy reaction type product, β-hydroxy ester, in low yield.