Harel Tal, Rozen Shlomo
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel.
J Org Chem. 2007 Aug 17;72(17):6500-3. doi: 10.1021/jo0709450. Epub 2007 Jul 18.
Alpha-alkyl amino acids can be efficiently prepared in high yields from the respective amino acids themselves. The key step is the oxidation of the amine function to create the corresponding alpha-nitro acid in a fast and very high yield reaction followed by phase-transfer alkylation and finally reduction to the desired alpha-alkyl amino acid. Several such acids containing aromatic rings or additional carboxylic groups and acids with steric hindrance at the alpha-position are suitable substrates. Several alkyl halides were examined as alkylating agents.
α-烷基氨基酸可以从相应的氨基酸本身高效高产率地制备。关键步骤是将胺官能团氧化，在快速且高产率的反应中生成相应的α-硝基酸，随后进行相转移烷基化，最后还原为所需的α-烷基氨基酸。几种含有芳环或额外羧基的此类酸以及在α-位具有空间位阻的酸都是合适的底物。研究了几种卤代烷作为烷基化剂。
