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Asymmetric Synthesis of (S)‐2‐Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis
ChemCatChem ( IF 3.8 ) Pub Date : 2011-01-21 , DOI: 10.1002/cctc.201000435
Ben de Lange , David J. Hyett , Peter J. D. Maas , Daniel Mink , Friso B. J. van Assema , Natascha Sereinig , André H. M. de Vries , Johannes G. de Vries

A tale of two catalysts: (S)‐2‐Indolinecarboxylic acid, an intermediate for ACE inhibitors, was until recently produced by Fischer indole synthesis and classical resolution in seven steps. However, Perkin condensation to form ortho‐chlorocinnamic acid, which is converted to (S)‐ortho‐chlorophenylalanine using the enzyme phenylalanine ammonia lyase prior to copper‐catalyzed ring closure thereof delivers the enantiopure product in just three steps.
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中文翻译:

生物催化和均相催化相结合不对称合成(S)-2-吲哚啉羧酸

两种催化剂的故事:S)-2-吲哚啉羧酸,一种ACE抑制剂的中间体,直到最近由Fischer吲哚合成和经典拆分工艺分七个步骤生产。但是,珀金族缩合形成氯肉桂酸,然后使用苯丙氨酸氨裂合酶将其转化为(S)-氯苯丙氨酸,然后铜催化闭环,只需三步即可得到对映体纯产物。
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更新日期:2011-01-21
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