Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds
Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds
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DOI：
10.1002/anie.201605754
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发表时间：
2016-10-04
影响因子：
16.6
通讯作者：
Yudin, Andrei K.
中科院分区：
文献类型：
--
作者：
Diaz, Diego B.;Scully, Conor C. G.;Yudin, Andrei K.
在这里，我们证明了使用-硼醛和酰基硼酸酯在合成氨基硼酸衍生物。这项工作突出了硼取代亚胺离子的未开发潜力，并提供了深入了解N-甲基亚氨基二乙酰基（MIDA）硼酸盐在缩合和互变异构过程中的行为。这一贡献的制备价值在于证明，各种胺，包括线性和环状肽，可以很容易地与含硼片段共轭。氨基MIDA-硼酸盐的温和脱保护使得能够以高化学产率获得-和-氨基硼酸。这一简单的过程应适用于合成广泛的生物活性分子以及交叉偶联反应的前体。
Herein, we demonstrate the use of -boryl aldehydes and acyl boronates in the synthesis of aminoboronic acid derivatives. This work highlights the untapped potential of boron-substituted iminium ions and offers insights into the behavior of N-methyliminodiacetyl (MIDA) boronates during condensation and tautomerization processes. The preparative value of this contribution lies in the demonstration that various amines, including linear and cyclic peptides, can be readily conjugated with boron-containing fragments. A mild deprotection of amino MIDA-boronates enables access to - and -aminoboronic acids in high chemical yields. This simple process should be applicable to the synthesis of a wide range of bioactive molecules as well as precursors for cross-coupling reactions.