Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)†,Chemical Science

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Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)†
Chemical Science ( IF 7.6 ) Pub Date : 2018-05-16 00:00:00 , DOI: 10.1039/c8sc01486h
Tomoya Shiro ₁ , Anne Schuhmacher ₁ , Moritz K Jackl ₁ , Jeffrey W Bode ₁

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We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.

中文翻译：

通过三氟硼酸亚胺 (TIM) 从胺和酰基三氟硼酸钾 (KAT) 轻松合成 α-氨基硼酸†

我们报道了从酰基三氟硼酸钾（KAT）容易形成三氟硼酸亚胺（TIM），以及通过还原或格氏加成将TIM转化为α-氨基三氟硼酸盐。建立了α-氨基三氟硼酸盐水解为α-氨基硼酸的条件，α-氨基硼酸是重要的生物活性化合物。这种新方法允许获得空间要求高的 α-氨基硼酸，而目前可用的方法不易制备这些α-氨基硼酸。这项工作还介绍了易于制备和处理的TIM，作为一类新的官能团，可作为有价值的有机化合物的前体。

更新日期：2018-05-16

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