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Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides.
Chemistry - An Asian Journal ( IF 4.1 ) Pub Date : 2020-05-26 , DOI: 10.1002/asia.202000503
Xiangqiang Li 1 , Mingyi Jiang 1 , Tangyu Zhan 1 , Weidi Cao 1 , Xiaoming Feng 1
Affiliation  

A highly enantioselective three‐component hydroacyloxylation/1,4‐conjugate addition of ortho ‐hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′ ‐dioxide/Sc(OTf)3 complex, which went through in situ generated ortho ‐quinone methides with α‐acyloxyenamides, delivering a range of corresponding chiral α‐acyloxyenamides derivatives containing gem (1,1)‐diaryl skeletons in moderate to good yields with excellent ee values. The scale‐up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X‐ray crystal structure of the α‐acyloxyenamide intermediate and product.

中文翻译:

酰胺的催化不对称三组分氢酰氧基化/ 1,4-共轭加成反应。

一种高度对映体选择性三组分hydroacyloxylation / 1,4-共轭加成的羟基苄基醇,ynamides和羧酸是在一个手性的存在下在温和的反应条件下发育N,N'二氧化物/ SC(OTF)3配合物,通过原位生成的苯醌甲基化物与α-酰氧基烯酰胺一起,以中等至良好的产率提供了一系列相应的含有宝石(1,1)-二芳基骨架的手性α-酰氧基酰胺衍生物,并具有出色的ee价值观。放大实验和进一步推导表明了该催化系统的实用性。此外,提出了一种可能的催化循环和过渡态模型,以基于α-酰亚氧酰胺中间体和产物的X-射线晶体结构阐明立体选择性的起源。
更新日期:2020-07-01
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