Chemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminases,Advanced Synthesis & Catalysis

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Chemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminases
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-09 , DOI: 10.1002/adsc.202000798
Daniel González‐Martínez ₁ , Vicente Gotor ₁ , Vicente Gotor‐Fernández ₁

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A series of amino alcohols have been prepared in a chemo‐, diastereo‐ and enantioselective fashion starting from the corresponding (het)aryl diketones, avoiding tedious chemical protection and deprotection steps. Different alcohol dehydrogenases have been able to selectively reduce the more reactive trifluoroacetyl groups under optimized conditions, while amine transaminases catalyzed the biotransamination of the less hindered acetyl groups. Based on the different reactivity of the acetyl and trifluoroacetyl groups, the design of sequential and concurrent cascades was investigated. The proper selection of the enzymes permits the synthesis of amino alcohol stereoisomers in high to excellent yields (86–>99% conversion) and remarkable stereocontrol (up to >99% de and >99% ee) using an aqueous medium and mild reaction conditions.

中文翻译：

通过使用醇脱氢酶和胺转氨酶的一锅反应，化学和立体选择性地合成氟化氨基醇

从相应的（杂）芳基二酮开始，以化学，非对映和对映选择性的方式制备了一系列氨基醇，避免了繁琐的化学保护和脱保护步骤。在优化条件下，不同的醇脱氢酶已经能够选择性地还原反应性更高的三氟乙酰基，而胺转氨酶则催化了受阻较少的乙酰基的生物转氨作用。基于乙酰基和三氟乙酰基的不同反应性，研究了级联和并发级联的设计。正确选择酶可以合成氨基醇立体异构体，产率高至极好（86-> 99％的转化率）和出色的立体控制（de > 99％和ee > 99％））使用水性介质和温和的反应条件。

更新日期：2020-09-09

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