手性磷酸催化的环戊烯二酮通过中氮茚的傅克共轭加成反应实现去对称化
Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel-Crafts Conjugate Addition of Indolizines.
作者信息
Ni Qijian, Zhu Zhiming, Fan Yanjun, Chen Xiaoyun, Song Xiaoxiao
机构信息
Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, Anhui, P. R. China.
Jiangsu University of Science and Technology, School of Environmental and Chemical Engineering, No. 2 Mengxi Road, Zhenjiang, Jiangsu, 212003, P. R. China.
出版信息
Org Lett. 2021 Dec 17;23(24):9548-9553. doi: 10.1021/acs.orglett.1c03780. Epub 2021 Dec 2.
An organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62-91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp C-H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
已成功开发出一种有机催化的、高度非对映和对映选择性的中氮茚对前手性环戊烯二酮的傅克共轭加成反应。这种去对称转化为所需的中氮茚取代的环戊二酮提供了直接的合成方法，产率为62 - 91%，且具有优异的立体选择性。通过还原或氧化等多种后期官能团化反应证明了该方法的实用性。重要的是，在一锅法中用硝基甲烷进行直接的sp C-H官能团化反应生成了带有远程手性中心的中氮茚连接的轴向手性苯乙烯。
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