Chelating Picolinaldehyde Hydrazone Amides as Protecting Groups for Carboxylic Acids: Orthogonal Reactivities of Hydrazone Amides and Esters in Hydrolysis
作者:Yasuhiro Nishikawa、Daiki Mori、Mayuko Toyoda、Yukiho Amano、Midori Hosoi、Momoka Ando、Osamu Hara
DOI:10.1021/acs.orglett.2c03670
日期:2023.2.17
We report a chelating hydrazone amide as a protecting group for carboxylic acids. Unlike most esters, 2-picolinaldehyde hydrazone amides are stable under acidic or basic hydrolytic conditions. However, hydrazone amides can be easily converted to the corresponding carboxylic acids via Ni-mediated hydrolysis. Orthogonal reactivities of the hydrazone amides and representative protecting groups were verified
我们报告了螯合腙酰胺作为羧酸的保护基团。与大多数酯不同,2-吡啶甲醛腙酰胺在酸性或碱性水解条件下稳定。然而,通过 Ni 介导的水解,腙酰胺可以很容易地转化为相应的羧酸。通过对照实验和肽合成验证了腙酰胺和代表性保护基团的正交反应性,表明螯合腙酰胺是非常有用的保护基团。