Scalable Synthesis of Vicinal Quaternary Stereocenters via the Solid-State Photodecarbonylation of a Crystalline Hexasubstituted Ketone

被引：11
|
作者：
Chang, Trevor Y. [1 ]
Dotson, Jordan J. [1 ]
Garcia-Garibay, Miguel A. [1 ]
机构：
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 22期
基金：
美国国家科学基金会;
关键词：
NANOCRYSTALLINE SUSPENSIONS; GREEN CHEMISTRY; REACTIVITY;
D O I：
10.1021/acs.orglett.0c03226
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the synthesis and stereospecific solid-state photodecarbonylation of a hexasubstituted ketone featuring six distinct alpha-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 alpha-substituents having orthogonal chemical reactivity illustrate the potential of this transformation toward constructing complex architectures.
引用
收藏
页码：8855 / 8859
页数：5
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