Phosphorylation Organocatalysts Highly Active by Design.,Organic Letters

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Phosphorylation Organocatalysts Highly Active by Design.
Organic Letters ( IF 4.9 ) Pub Date : 2020-04-22 , DOI: 10.1021/acs.orglett.0c01226
Amit Fallek ₁ , Mor Weiss-Shtofman ₁ , Maria Kramer ₁ , Roman Dobrovetsky ₁ , Moshe Portnoy ₁

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The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

中文翻译：

磷酸化有机催化剂的设计具有高活性。

通过将低聚醚附加物连接到咪唑基或氨基吡啶基活性单元上的苄基取代基上，可以增强醇/苯酚磷酸化的亲核有机催化剂的活性，这可能是因为稳定了醚氧与带正电的氮杂杂环的正离子相互作用。催化中间体，并且大大高于一系列底物的已知基准催化剂。密度泛函理论计算和对这种稳定相互作用潜力较低的类似物的研究支持了我们的假设。

更新日期：2020-04-22

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