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Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2018-01-10 , DOI: 10.1021/jacs.7b11299
Matthew R Porter 1 , Rami M Shaker 1 , Cristian Calcanas 1 , Joseph J Topczewski 1
Affiliation  

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

中文翻译:

烯丙基叠氮化物的立体选择性动态环化:四氢化萘、色满和四氢喹啉的合成

该报告描述了通过串联烯丙基叠氮化物重排/Friedel-Crafts 烷基化立体选择性合成 3-叠氮基-四氢化萘、-苯并二氢吡喃和-四氢喹啉。事实证明,将带有三氯乙酰亚胺酯侧链的烯丙基叠氮化物暴露于催化量的 AgSbF6 中对于这种转化是最佳的。该级联成功区分了平衡叠氮化物异构体,提供了具有优异产率和选择性的产品(>25 个示例,高达 94% 的产率和 >25:1 dr)。在许多情况下,反应异构体仅占平衡混合物的微量部分,敏锐地说明了这些系统的动态性质。我们通过合成哈苏巴南(hasubanan)展示了该过程的实用性。
更新日期:2018-01-10
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