Nature Communications ( IF 14.7 ) Pub Date : 2022-09-26 , DOI: 10.1038/s41467-022-33411-9 Yao Zhang 1 , Deyong Qiao 1 , Mei Duan 1 , You Wang 1 , Shaolin Zhu 1, 2
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Chiral α-aminoboronic acids and their derivatives are generally useful as bioactive compounds and some have been approved as therapeutic agents. Here we report a NiH-catalysed asymmetric hydroamidation process that with a simple amino alcohol ligand can easily produce a wide range of highly enantioenriched α-aminoboronates from alkenyl boronates and dioxazolones under mild conditions. The reaction is proposed to proceed by an enantioselective hydrometallation followed by an inner-sphere nitrenoid transfer and C–N bond forming sequence. The synthetic utility of this transformation was demonstrated by the efficient synthesis of a current pharmaceutical agent, Vaborbactam.
中文翻译：
NiH催化烯基硼酸酯不对称加氢酰胺化对映选择性合成α-氨基硼酸酯
手性 α-氨基硼酸及其衍生物通常用作生物活性化合物，有些已被批准用作治疗剂。在这里，我们报告了一种 NiH 催化的不对称氢酰胺化过程，该过程使用简单的氨基醇配体可以在温和条件下从烯基硼酸酯和二恶唑酮轻松生产各种高度对映体丰富的 α-氨基硼酸酯。建议该反应通过对映选择性加氢金属化反应进行，然后进行内球形氮转移和 C-N 键形成序列。这种转化的合成效用通过当前药物 Vaborbactam 的有效合成得到证明。
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