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一种基于Aza-Prilezhaev的方法,用于在立体特异性1,2-氨基基基1,2-氨基基化中逆转区域选择性

Wenbin Tu^1,2, Joshua J Farndon², Craig M Robertson¹

¹Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD.

Angewandte Chemie (International ed. in English)

|August 22, 2024

概括

这项研究引入了一种用于立体特异性烯功能化的新方法. 在酸性条件下,BocNHOT可实现高效的1,2-氨基化和相关反应,具有独特的区域选择性.

科学领域:

有机化学有机化学
合成方法论合成方法论
立体选择性合成立体选择性合成

背景情况:

基的1,2-氨基氧化是有机合成中的关键转化.
现有的方法往往在区域选择性和立体化学控制方面面临局限性.

研究的目的:

开发一种新型的试剂系统,用于基的立体特异性1,2-氨基氧化.
探索这个新合成协议的范围和区域化学结果.

主要方法:

在酸性条件下 (三酸,TFA) 在水的存在下使用BocNHOT.
研究涉及S_N2开放的分子间aza-Prilezhaev亚齐里丁化反应机制.

主要成果:

高效率地实现了基的立体特异性1,2-氨基氧化.
与环氧化启动的协议相比,已证明的区域化学结果相反或更有选择性.
扩大了反应范围,包括1,2-amino(thio) etherification,diamination,aminoazidation和aminofluorination的其他核素.
展示了分子内反应的可行性,包括类似于azabicyclobutane的转化.

结论:

博克NHOTs/TFA/水系统为立体选择性烯功能化提供了一个强大而通用的平台.
这种方法为现有方法提供了补充的区域选择性,扩大了合成可能性.
开发的协议通过各种核替代物促进了对各种含化合物的获取.

关键词:

阿尔肯斯 (Alkenes) 是一种类型.氨基氧化氨基氧化.小环化合物是一种小环化合物.合成方法合成方法乌姆波隆格 (Umpolung) 是一个古老的城市.

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