Enantioselective Synthesis of α-Amino Acids by Chiral Phase-Transfer Catalysis
Enantioselective Synthesis of α-Amino Acids by Chiral Phase-Transfer Catalysis
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手性相转移催化对映选择性合成 α-氨基酸
DOI：
10.1002/chin.200421268
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发表时间：
2003
期刊：
影响因子：
--
通讯作者：
K. Maruoka
中科院分区：
文献类型：
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作者：
T. Ooi;K. Maruoka
α-氨基酸是最重要的天然氨基酸，具有广泛的生物学功能，因此开发一种高效、可靠的方法来制备具有足够结构多样性的光学活性α-氨基酸及其衍生物一直是一个令人感兴趣的领域。本文综述了手性相转移催化剂在实验室制备光学活性α-氨基酸的不对称方法。研究表明，立体选择性功能化是合成的关键过程以金鸡纳碱衍生的季铵盐或纯合成的手性铵盐为催化剂，通过α-氨基酸酯（包括甘氨酸叔丁酯）的Schiff碱（烷基化、Michael加成、羟醛缩合反应），α-二烷基-α-氨基酸和β-羟基-α-氨基酸。此外，高立体选择性的N-末端烷基化的席夫碱激活肽的手性相转移催化也被描述。
α-Amino acids are the most important naturally occurring amino acids assembling into polypeptides with a wide range of vital biological functions, and hence the development of an efficient and reliable method for the preparation of optically active α-amino acids and their derivatives with sufficient structural diversity has been a field of considerable interest. Main purpose of this review is to illustrate the range of asymmetric approaches available for the laboratory preparation of optically active α-amino acids by using chiral phase-transfer catalysts. The key process is revealed to be stereoselective functionalization (alkylation, Michael addition, aldol reaction) of the Schiff base of α-amino acid esters including glycine tert-butyl ester with either cinchona alkaloid-derived quaternary ammonium salts or purely synthetic chiral ammonium salts as catalyst, providing a practical route to a variety of optically active α-alkyl-α-amino acids, α, α-dialkyl-α-amino acids and β-hydroxy-α-amino acids. In addition, highly stereoselective N-terminal alkylation of Schiff base-activated peptides by chiral phase-transfer catalysis is also described.