A One Pot Procedure for the Synthesis of α-Hydroxyamides from the Corresponding α-Hydroxyacids

Abstract

α-Hydroxyamides are synthesized from the cooresponding α-hydroxyacids by generation of the bis-trimethylsilyl derivative and treating it with oxalyl chloride. Following addition of the appropriate amine, the TMS ether is hydrolyzed in the workup to provide the desired α-hydroxyamide. As summarized in Table I, this reaction has proven to be general and compatible with chiral α-hydroxyacids affording the desired α-hydroxyamides in excellent yield (77–99%).