UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Belfield, Dublin 4, Ireland.
Amino Acids. 2010 Aug;39(3):849-58. doi: 10.1007/s00726-010-0541-3. Epub 2010 Mar 12.
An atom-efficient and stereoselective synthesis has been developed for the preparation of alpha-2H-labelled (S)-alpha-amino acids, starting from a novel chiral diketopiperazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1,4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure alpha-amino acids.
已经开发出一种高效、立体选择性的合成方法，用于制备 α-2H 标记的 (S)-α-氨基酸，起始原料为新型手性二酮哌嗪骨架。手性模板的高效单烷基化反应得到 (S)-取代的加合物，亲电试剂的性质对立体化学结果有显著影响。随后的烷基化反应完全具有选择性，仅生成 1,4-顺式加合物作为唯一的非对映异构体。使用硝酸铈铵进行脱保护，然后进行酸水解，得到对映纯的 α-氨基酸。
