Carbene-catalyzed chirality-controlled site-selective acylation of saccharides

酰化 卡宾 选择性 手性(物理) 化学 分子内力 催化作用 组合化学 有机合成 有机化学 立体化学 物理 量子力学 Nambu–Jona Lasinio模型 夸克 手征对称破缺
作者
Ying‐Guo Liu,Zhixiong Zhong,Yuyang Tang,Hongling Wang,Sai V. C. Vummaleti,Xi Peng,Peng Shi,Xinglong Zhang,Yonggui Robin
出处
期刊:Nature Communications [Nature Portfolio]
卷期号:16 (1)
标识
DOI:10.1038/s41467-024-55282-y
摘要

Acylation stands as a fundamental process in both biological pathways and synthetic chemical reactions, with acylated saccharides and their derivatives holding diverse applications ranging from bioactive agents to synthetic building blocks. A longstanding objective in organic synthesis has been the site-selective acylation of saccharides without extensive pre-protection of alcohol units. In this study, we demonstrate that by simply altering the chirality of N-heterocyclic carbene (NHC) organic catalysts, the site-selectivity of saccharide acylation reactions can be effectively modulated. Our investigation reveals that this intriguing selectivity shift stems from a combination of factors, including chirality match/mismatch and inter- / intramolecular hydrogen bonding between the NHC catalyst and saccharide substrates. These findings provide valuable insights into catalyst design and reaction engineering, highlighting potential applications in glycoside analysis, such as fluorescent labelling, α/β identification, orthogonal reactions, and selective late-stage modifications. The site-selective acylation of saccharides without extensive pre-protection of alcohol units has been a longstanding objective in organic synthesis. Here, the authors demonstrate that by simply altering the chirality of N-heterocyclic carbene (NHC) organic catalysts, the site-selectivity of saccharide acylation can be effectively modulated.
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