Synthesis of α-Aminonitriles via Ammonium-Catalyzed Reactions of Aminoacetonitrile,Journal of the American Chemical Society

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Synthesis of α-Aminonitriles via Ammonium-Catalyzed Reactions of Aminoacetonitrile
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-09-12 , DOI: 10.1021/jacs.4c09789
Xiangyuan Liu ₁ , Yu Deng ₁ , Tianran Deng ₁ , Yang Yu ₁ , Yuhong Gao ₁ , Xiang-Lei Han ₁ , Cheng Cheng ₁ , Jisheng Luo ₁ , Li Deng _{1,

2}

Affiliation

α-Aminonitriles are not only broadly useful building blocks but also structural motifs in bioactive molecules. The Strecker reaction is one of the most widely used methods for α-aminonitrile synthesis. However, a severe drawback in Strecker reactions is the required use of a stoichiometric amount of toxic cyanation reagents. Thus, the development of a greener and widely applicable method for the synthesis of aminonitriles from readily available starting materials presents an important yet unmet challenge. We developed a general and new method for the synthesis of aminonitriles from readily available aminoacetonitrile. This method utilized off-the-shelf ammonium salts as catalysts, tolerated air and moisture, and avoided the use of cyanation reagents, which rendered it a greener alternative to the widely practiced Strecker reaction approach. We further illustrated that chiral ammonium-catalyzed asymmetric reactions of N-arylidene aminoacetonitriles could provide chiral α-tertiary and α-quaternary aminonitriles and α-aminonitriles bearing two continuous stereocenters.

中文翻译：

氨基乙腈的铵催化反应合成 α-氨基腈

α-氨基腈不仅是广泛有用的构建单元，而且还是生物活性分子的结构基序。 Strecker反应是最广泛使用的α-氨基腈合成方法之一。然而，Strecker 反应的一个严重缺点是需要使用化学计量的有毒氰化试剂。因此，开发一种更环保且广泛适用的方法，从容易获得的起始原料合成氨基腈，提出了一个重要但尚未解决的挑战。我们开发了一种从容易获得的氨基乙腈合成氨基腈的通用新方法。该方法利用现成的铵盐作为催化剂，耐受空气和水分，并避免使用氰化试剂，这使其成为广泛应用的 Strecker 反应方法的更环保的替代方法。我们进一步说明， N-亚芳基氨基乙腈的手性铵催化不对称反应可以提供手性α-叔和α-季氨基腈以及带有两个连续立构中心的α-氨基腈。

更新日期：2024-09-17

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