Reactions of Alkyl Radicals with Oxime Ether: One-Pot Synthesis of α-Amino Acids

The addition of water-resistant carbon radicals to glyoxylic oxime ether provided a new method for the one-pot synthesis of α-amino acids via a carbon–carbon bond formation. The reaction of 2-hydroxy-2-methoxyacetic acid methyl ester with benzyloxyamine and an alkyl radical gave the protected α-amino acids via the stannyl radical-mediated reaction. In the absence of Bu3SnH, the predominant formation of the desired alkylated products was also observed by using RI and Et3B in boiling toluene. Et2Zn could serve as an initiator of these radical reactions as well as Et3B.