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Scalable Synthesis of Vicinal Quaternary Stereocenters via the Solid-State Photodecarbonylation of a Crystalline Hexasubstituted Ketone
Organic Letters ( IF 5.2 ) Pub Date : 2020-10-29 , DOI: 10.1021/acs.orglett.0c03226
Trevor Y. Chang 1 , Jordan J. Dotson 1 , Miguel A. Garcia-Garibay 1
Affiliation  

We report the synthesis and stereospecific solid-state photodecarbonylation of a hexasubstituted ketone featuring six distinct α-substituents. The photoproduct of the solid-state transformation features vicinal all-carbon quaternary stereocenters. While reactions carried out in bulk powders and aqueous crystalline suspensions were complicated by secondary photochemistry of the primary photoproduct, optimal conditions provided good yields and recyclable starting material. Subsequent transformations of the α-substituents having orthogonal chemical reactivity illustrate the potential of this transformation toward constructing complex architectures.

中文翻译:

通过晶体六取代酮的固态光脱羰基可缩放合成邻四元立体中心。

我们报告了具有六个不同的α-取代基的六取代酮的合成和立体定向固态光脱羰基。固态转变的光产物具有邻近的全碳四元立体中心。虽然在散装粉末和水性结晶悬浮液中进行的反应由于一次光产物的二次光化学而变得复杂,但最佳条件提供了良好的收率和可回收的原料。具有正交化学反应性的α-取代基的后续转化说明了这种转化对构建复杂结构的潜力。
更新日期:2020-11-21
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