吖内酯的动态动力学拆分反应研究进展

Research progress in dynamic kinetic resolution of azlactone

随着手性化合物研究与需求的快速发展,合成光学活性氨基酸这类重要的小分子化合物越来越被人们所重视.含氮杂环化合物吖内酯在亲核试剂的存在下,可以发生水解、醇解、硫解和胺解等反应,开环得到一系列手性氨基酸及其衍生物.同时,其结构中4位碳(C-4)上的氢原子具有酸性,在一定条件下能够发生烯醇互变,易外消旋化,因此是一类动态动力学拆分(DKR)的理想底物.文章综述了近年来吖内酯通过DKR反应制备光学纯氨基酸及其衍生物的研究进展.

With the rapid development of research and demand for chiral compounds,the synthesis of important small molecule compounds such as optically active amino acids has attracted more and more attention.In the presence of nucleophiles,azlactones with nitrogen-containing heterocyclic structures can undergo ring-opening reactions such as hydrolysis,alcoholysis,thiolysis,and amination to obtain a series of chiral amino acids and their derivatives.Besides,the hydrogen atom at the position of the 4-carbon(C-4)is acidic and can undergo enol interconversion under certain conditions to make racemization easy.Therefore,azlactones are ideal substrates for dynamic kinetic resolution(DKR)reactions.This review describes the recent research progress in preparation of chiral amino acids and their derivatives by DKR of azlactone.