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镍催化酰胺亲电试剂的对映选择性 Mizoroki-Heck 环化反应。

Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide electrophiles.

作者信息

Bulger Ana S, Nasrallah Daniel J, Tena Meza Arismel, Garg Neil K

机构信息

Department of Chemistry and Biochemistry, University of California at Los Angeles Los Angeles California 90095 USA

出版信息

Chem Sci. 2024 Jan 8;15(7):2593-2600. doi: 10.1039/d3sc05797f. eCollection 2024 Feb 14.

Abstract

Amide cross-couplings that rely on C-N bond activation by transition metal catalysts have emerged as valuable synthetic tools. Despite numerous discoveries in this field, no catalytic asymmetric variants have been disclosed to date. Herein, we demonstrate the first such transformation, which is the Mizoroki-Heck cyclization of amide substrates using asymmetric nickel catalysis. This proof-of-concept study provides an entryway to complex enantioenriched polycyclic scaffolds and advances the field of amide C-N bond activation chemistry.

摘要

依赖过渡金属催化剂进行C-N键活化的酰胺交叉偶联反应已成为有价值的合成工具。尽管该领域有众多发现,但迄今为止尚未公开催化不对称变体。在此,我们展示了首例此类转化,即使用不对称镍催化实现酰胺底物的 Mizoroki-Heck 环化反应。这项概念验证研究为合成复杂的对映体富集多环骨架提供了途径,并推动了酰胺C-N键活化化学领域的发展。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b90/10866352/a04faa8f7448/d3sc05797f-f1.jpg

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