Chiral Phosphoric Acid Catalyzed Asymmetric Addition of 2-(Vinyloxy)ethanol to Imines and Applications of the Products,Organic Letters

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Chiral Phosphoric Acid Catalyzed Asymmetric Addition of 2-(Vinyloxy)ethanol to Imines and Applications of the Products
Organic Letters ( IF 4.9 ) Pub Date : 2019-06-21 00:00:00 , DOI: 10.1021/acs.orglett.9b01970
Xudong Wu ₁ , Xi Yuan ₁ , Haijun Yang ₁ , Hua Fu ₁

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Chiral nitrogen-containing molecules such as chiral amines, azetidines, and 2-substituted tetrahydroquinolines are important privileged scaffolds in medicinal chemistry. In this paper, an efficient and highly enantioselective chiral phosphoric acid catalyzed asymmetric addition of 2-(vinyloxy)ethanol to imines has been developed for the first time, providing the corresponding chiral amines containing dioxolane acetals that can transform into useful chiral N-heterocycles including azetidines and 2-substituted tetrahydroquinolines with excellent optical purity.

中文翻译：

手性磷酸催化亚胺2-（乙烯基氧基）乙醇的不对称加成反应及其产物的应用

手性含氮分子，例如手性胺，氮杂环丁烷和2-取代的四氢喹啉是药物化学中重要的重要支架。本文首次开发了一种高效且高度对映体选择性的手性磷酸催化亚甲基2-（乙烯基氧基）乙醇的不对称加成反应，提供了相应的含有二氧戊环缩醛的手性胺，可以将其转化为有用的手性N-杂环，包括氮杂环丁烷和2-取代的四氢喹啉具有优异的光学纯度。

更新日期：2019-06-21

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