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镍催化烯酰胺的还原双碳官能化实现3,3-二烷基取代异吲哚啉酮的合成

Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides.

作者信息

Fang Ke, Huang Wenyi, Shan Chunxiao, Qu Jingping, Chen Yifeng

机构信息

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.

出版信息

Org Lett. 2021 Jul 16;23(14):5523-5527. doi: 10.1021/acs.orglett.1c01871. Epub 2021 Jun 28.

Abstract

Herein we report the nickel-catalyzed reductive dicarbofunctionalization of 1,1-disubstituted enamides with unactivated alkyl iodides to access the 3,3-dialkyl-substituted isoindolinone frameworks. This tandem cyclization/reductive coupling protocol exhibits broad functional group tolerance under mild conditions. The utilization of commercially accessible chiral Bn-Biox ligand allows excellent enantioselectivities to forge the tetrasubstituted stereocenters.

摘要

在此,我们报道了镍催化1,1-二取代烯酰胺与未活化的烷基碘进行还原双碳官能化反应,以构建3,3-二烷基取代的异吲哚啉酮骨架。这种串联环化/还原偶联方案在温和条件下表现出广泛的官能团耐受性。使用市售的手性Bn-Biox配体能够以优异的对映选择性构建四取代的立体中心。

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