Synthesis of Enol Adenosine 5'-Phosphate Derivatives by the Perkow Reaction of a Silylated Adenosine 5'-Phosphonate Derivative with α-Halo Ketones

This paper deals with the synthesis of α-substituted enol ester derivatives of adenosine 5'- phosphate. These compounds were formed by the Perkow reaction of α-chloromethyl ketones with an in situgenerated adenosine-5'-yl bis(trimethylsilyl) phosphite intermediate. Among these reactions, the use of α- chloro-2',4'-difluoroacetophenone gave predominantly the enol phosphate derivative over the Arbuzov reaction product and the carbonyl adduct, which were formed as byproducts.