Formal one-carbon insertion into esters via copper-catalyzed diyne cyclization/[1,2]-acyl shift†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-10-09 DOI:10.1039/D4QO01623H

Chong-Yang Shi, Qian Wang, Li-Gao Liu, Jing Wang, Rui Chen, Lin Liu, Long-Wu Ye, Xin Lu and Xin-Qi Zhu

引用次数: 0

Abstract

Transition metal-catalyzed formal one-carbon insertion into carbonyl compounds is an efficient method for the preparation of complex molecules. Herein, we report a copper-catalyzed intramolecular formal one-carbon insertion into esters through a cascade diyne cyclization/[1,2]-acyl shift pathway, enabling the atom-economical synthesis of various chromeno[3,4-c]pyrroles bearing quaternary carbon stereocenters under mild reaction conditions. Moreover, moderate enantioselectivities are achieved in the catalytic asymmetric formal one-carbon insertion. The reaction mechanism is illustrated through computational studies.

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通过铜催化二炔环化/[1,2]-酰基转移将单碳正式插入酯中

过渡金属催化的形式一碳插入羰基化合物是制备复杂分子的有效方法。在此，我们报告了一种铜催化的分子内形式一碳插入酯的方法，该方法通过级联二炔环化/[1,2]-酰基转移途径，在温和的反应条件下以原子经济的方式合成了各种带有季碳立体中心的色烯并[3,4-c]吡咯。此外，在催化不对称形式一碳插入中还获得了适度的对映选择性。计算研究说明了该反应的机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.