Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids.,Angewandte Chemie International Edition

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Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-09-09 , DOI: 10.1002/anie.202009892
Kai Wang ₁ , Jianliang Yu ₁ , Ying Shao ₁ , Shengbiao Tang ₁ , Jiangtao Sun ₁

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The asymmetric synthesis of β^2,2‐amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O‐acetals is reported, providing β^2,2‐amino esters bearing an all‐carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter‐anion‐directed catalysis. As a result, a concise, practical, and atom‐economic protocol toward rapidly access to β^2,2‐amino acids has been developed.

中文翻译：

通过有机催化的氨甲基化形成全碳四元立体中心：精确获得β2,2-氨基酸。

的β不对称合成^2,2- α-氨基酸保留在有机合成一个巨大的挑战。这里有稳定且容易获得的N，O-缩醛烯酮的一种新颖的对映选择性有机催化氨基甲基报道，提供β ^2,2-氨基酯轴承在高对映体比率的全碳季立体中心具有手性磷酸催化量。通常，这种转变可能是通过不对称的反阴离子导向催化进行的。其结果是，一个简洁，实用，和原子的经济朝向快速访问β协议^2,2 α-氨基酸已经研制成功。

更新日期：2020-09-09

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