A novel method of nucleophilic addition to the alpha carbon of an enol ether has been recently discovered and explored. This method utilized mildly acidic conditions to promote the formation of a presumed oxyallyl cation intermediate, which is readily trapped by various carbon nucleophiles, therefore, showcasing a wide range of substrate compatibility. The notable aspect of this method is that the enol ether functionality inherent in the starting material remains intact when subjected to these conditions. Overall, this chemistry demonstrates a rare example of nucleophilic substitution reaction involving an intermediacy oxyallyl cation.

Functionalization of enol ether at the alpha position

248th National Meeting (2014)

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