Enantioselective Synthesis of Chiral Seven-Membered Ring via Rh-Catalyzed 1,4-Addition of Arylboronic Acids to Enones

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-04-23 DOI:10.1039/d5qo00444f

Ren-Rong Liu, Hao-Ran Wang, Wen-Guang Zhou, Li-Wen Zhan, Long-Long Xi

引用次数: 0

Abstract

A rhodium-catalyzed reaction between enones and arylboronic acids has been developed to construct chiral seven-membered ring through enantioselective 1,4-addition. This reaction offers outstanding functional group compatibility and excellent regio-, and enantiooselectivities using easily accessible arylboronic acids. Furthermore, to confirm the practicality of the reaction and understand its mechanism, we conducted in-depth studies on both product transformations and reaction pathways. This method demonstrates numerous advantages, including mild reaction conditions, readily available catalysts and ligands, a broad range of substrates, and the potential for synthesizing similar scaffolds of natural products.

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铑催化1,4-芳基硼酸加成烯酮手性七元环的对映选择性合成

在铑催化下，烯酮与芳基硼酸通过对映选择性1,4加成形成手性七元环。该反应使用易于接近的芳基硼酸，具有出色的官能团相容性和优异的区域和对映体选择性。此外，为了确认反应的实用性和了解其机理，我们对产物转化和反应途径进行了深入的研究。该方法具有许多优点，包括反应条件温和，催化剂和配体容易获得，底物范围广泛，以及合成类似天然产物支架的潜力。

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.