Zhang Yinfeng, Farrants Helen, Li Xuechen
Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Rd., Hong Kong (China), Fax: (+852) 28571586.
Chem Asian J. 2014 Jul;9(7):1752-64. doi: 10.1002/asia.201400111. Epub 2014 May 19.
β-Hydroxy-α-amino acids are not only used by synthetic chemists but are also found in natural products, many of which show anti-microbial or anti-cancer properties. Over the past 30 years, chemists have searched for many asymmetric routes to these useful building blocks. Initial attempts to synthesize these compounds utilized chiral auxiliaries and the reactions of glycine equivalents with aldehydes to form two stereocenters in one step. Other methods with the formation of specific intermediates or that were aimed at a specific amino acid have also been investigated. Asymmetric hydrogenation by dynamic kinetic resolution has emerged as a high-yielding method for the synthesis of an array of modified amino acids with good stereoselectivity. More recently, amino-acid functionalization and multicomponent reactions have increased the atom economy and simplified many long and difficult routes. In this Focus Review, many of the elegant syntheses of these compounds are explored. The applications of β-hydroxy-α-amino acids in natural-product synthesis are also mentioned.
β-羟基-α-氨基酸不仅被合成化学家所使用，在天然产物中也能找到，其中许多天然产物具有抗菌或抗癌特性。在过去30年里，化学家们探寻了许多合成这些有用结构单元的不对称方法。最初合成这些化合物的尝试利用了手性助剂以及甘氨酸等价物与醛的反应，一步形成两个立体中心。还研究了其他形成特定中间体或针对特定氨基酸的方法。通过动态动力学拆分进行的不对称氢化已成为一种高产率方法，可用于合成一系列具有良好立体选择性的修饰氨基酸。最近，氨基酸官能化和多组分反应提高了原子经济性，简化了许多冗长且困难的合成路线。在本重点综述中，探讨了这些化合物的许多精妙合成方法。还提到了β-羟基-α-氨基酸在天然产物合成中的应用。
