A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise beta-Amino Acid Esters
A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise beta-Amino Acid Esters
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结合氨解解析和 Aza-Michael 加成的单一脂肪酶催化一锅法：一种简单有效的合成 β-氨基酸酯的方法
DOI：
10.1002/ejoc.201500760
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发表时间：
2015
影响因子：
2.8
通讯作者：
Wu Qi
中科院分区：
文献类型：
--
作者：
Xu Fan;Wu Qiongsi;Chen Xiaoyang;Lin Xianfu;Wu Qi
开发了一种结合氮杂迈克尔加成和氨解拆分的新型一锅法，以来自南极假丝酵母的脂肪酶 B（CAL-B）作为唯一催化剂获得手性 β-氨基酸酯。该方法反应条件温和，操作简便。经过一系列详细的优化研究，通过这一一锅法，成功合成了 10 种外消旋芳香胺或脂肪胺，并成功合成了 12 种手性 β-氨基酸酯和 10 种手性酰胺，理论收率优异。放大过程也有效，反应速率或对映选择性没有明显降低，这使得该方法适合大规模生产手性 β-氨基酸酯。
A novel one‐pot protocol combining aza‐Michael addition and aminolysis resolution was developed to obtain chiral β‐amino acid esters with lipase B fromCandida antarctica(CAL‐B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one‐pot procedure, and twelve chiral β‐amino acid esters and ten chiral amides were successfully synthesised with excellenteevalues in theoretical yields. Scaled‐up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large‐scale production of chiral β‐amino acid esters.