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The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Brønsted Acids
Synlett ( IF 1.7 ) Pub Date : 2018-08-28 , DOI: 10.1055/s-0037-1610262 William Wulff 1 , Xin Zhang , Yijing Dai
Synlett ( IF 1.7 ) Pub Date : 2018-08-28 , DOI: 10.1055/s-0037-1610262 William Wulff 1 , Xin Zhang , Yijing Dai
Affiliation
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An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
中文翻译：
路易斯酸或布朗斯台德酸加速α-羟基醛亚胺的重排
开发了一种从 α-羟基亚胺合成 α-氨基酮的有效方法。该反应通过 α-亚胺醇重排发生，包括甲醇碳的取代基迁移到亚胺碳。发现最佳催化剂是硅胶或蒙脱石 K 10，它们以高产率影响各种芳基和烷基取代基的迁移。重排也可以在由醛和胺原位生成的亚胺上进行，其产率与由预先形成的亚胺的产率基本相同。
更新日期：2018-08-28
中文翻译：
路易斯酸或布朗斯台德酸加速α-羟基醛亚胺的重排
开发了一种从 α-羟基亚胺合成 α-氨基酮的有效方法。该反应通过 α-亚胺醇重排发生，包括甲醇碳的取代基迁移到亚胺碳。发现最佳催化剂是硅胶或蒙脱石 K 10，它们以高产率影响各种芳基和烷基取代基的迁移。重排也可以在由醛和胺原位生成的亚胺上进行，其产率与由预先形成的亚胺的产率基本相同。
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