Metal-Free C–H Functionalization of Allenamides: An Access to Branched Allylic Esters

A regioselective acyloxylation with carboxylic acids at the proximal carbon of allenamides by an N-iodosuccinimide-mediated C–H functionalization is reported. The reaction proceeds rapidly, is scalable to a gram scale, and displays a broad substrate scope, providing an efficient and practical protocol for the synthesis of branched allylic esters. Notably, protected amino acids were tolerated under the reaction conditions and afforded allylic amino acid esters in moderate yields.

本文报道了一种由N-碘代丁二酰亚胺（N-iodosuccinimide）介导的C-H官能化（C–H functionalization）反应，可在联烯酰胺（allenamides）的近端碳位上与羧酸发生区域选择性酰氧基化。该反应速率快捷，可放大至克级规模，且底物适用范围宽泛，为支链烯丙基酯的合成提供了高效且实用的合成方案。值得注意的是，受保护的氨基酸在该反应条件下具备良好耐受性，可获得中等收率的烯丙基氨基酸酯类产物。