Synthesis of chiral α-amino-diazoketones on solid support:: an access to β-homologated amino acid derivatives

Diazoketone derivatives were obtained on solid support from their corresponding a-amino acids anchored by their N-terminus to the resin. A complete study was performed to optimize the two steps process of this synthesis on solid support: activation of the carboxylic acid function followed by reaction with diazomethane. The obtained diazoketones were then submitted to Wolff rearrangement in the presence of an amine to yield the corresponding homologated amides or in the presence of water to yield the corresponding beta-homologated amino acids.