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Synthesis of β-Carbonyl α-Iminoamides by Double Insertion of Isocyanides into Aldehydes
Organic Letters ( IF 4.9 ) Pub Date : 2024-07-24 , DOI: 10.1021/acs.orglett.4c01871
Di Lu 1 , Shaohang Lu 1 , Chang-Hua Ding 2 , Xinyao Li 1 , Bin Xu 3, 4, 5
Affiliation  

An unprecedented trimethylsilyl trifluoromethanesulfonate (TMSOTf)-promoted selective double insertion of isocyanides into aldehydes was developed, providing an efficient protocol for synthetically challenging β-carbonyl α-iminoamides. The given approach is applicable for a diverse selection of readily accessible aldehydes, along with isocyanides serving as essential precursors for “amide” and “imine” scaffolds. The versatile transformations of the given products were demonstrated, and the pivotal intermediates for the plausible mechanism were identified.

中文翻译:


异氰化物双插入醛合成β-羰基α-亚氨基酰胺



开发了一种前所未有的三氟甲磺酸三甲基硅酯(TMSOTf)促进异氰化物选择性双插入醛中,为合成具有挑战性的β-羰基α-亚氨基酰胺提供了有效的方案。给定的方法适用于多种容易获得的醛,以及作为“酰胺”和“亚胺”支架的重要前体的异氰化物。展示了给定产物的多功能转化,并确定了合理机制的关键中间体。
更新日期:2024-07-26
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