Catalytic Approach to Diverse α‐Aminoboronic Acid Derivatives by Iridium‐Catalyzed Hydrogenation of Trifluoroborate‐Iminiums,Advanced Synthesis & Catalysis

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Catalytic Approach to Diverse α‐Aminoboronic Acid Derivatives by Iridium‐Catalyzed Hydrogenation of Trifluoroborate‐Iminiums
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-01-21 , DOI: 10.1002/adsc.202001350
Andrej Šterman ₁ , Janez Košmrlj ₂ , Nina Žigart ₃ , Stanislav Gobec ₁ , Izidor Sosič ₁ , Zdenko Časar _{1,

3}

Affiliation

A series of structurally diverse benzyl protected trifluoroborate‐ammoniums were prepared in good to high yields by an efficient hydrogenation of corresponding trifluoroborate‐iminiums using Crabtree's catalyst. Subsequent N‐ and B‐deprotections were demonstrated on selected examples to provide several α‐aminoboronic acids. Preliminary experiments on asymmetric version of the reaction indicated a correlation between E/Z‐ratio in the trifluoroborate‐iminium substrate and enantioselectivity. The broad scope, operational simplicity and efficiency of the presented method imply its high potential for a facile access to libraries of α‐aminoboronic acid derivatives that can be used in medicinal chemistry applications and beyond.

中文翻译：

三氟硼酸盐-铱的铱催化加氢催化合成多种α-氨基硼酸衍生物的方法

通过使用Crabtree催化剂对相应的三氟硼酸亚胺进行有效的加氢反应，制备了一系列结构多样的苄基保护的三氟硼酸亚铵。随后在选定的实例上证明了N和B脱保护基可提供几种α-氨基硼酸。对反应的不对称形式的初步实验表明，三氟硼酸亚胺底物的E / Z比与对映选择性之间存在相关性。所提出方法的广泛范围，操作简便性和高效性意味着其易于访问可用于药物化学应用及其他领域的α-氨基硼酸衍生物库的巨大潜力。

更新日期：2021-01-21

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