Development of a Method for the Preparation of α-Azido-Masked Acyl Cyanides, Synthetic Equivalents of N-Protected–C-Activated α-Amino Acids

A method for the preparation of α-azido-masked acyl cyanides as synthetic equivalents of N-protected–C-activated α-amino acids was developed using carbon–carbon bond formation between aldehydes and the Masked Acyl Cyanide Reagents, followed by sulfonylation and substitution by azide anion. This method was applied to the synthesis of d-threonine and l-allo-threonine derivatives.