沉淀驱动的非立体和区域选择性大环化：溶剂和烷基链长度的影响

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-10-03 DOI:10.1039/d5qo01179e

Kosuke Ono, Junya Fukumoto, Yu Tanoi, Hidetoshi Kawai

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引用次数: 0

摘要

研究了一种设计的双醛1与三苯骨架的苯并苯甲酸缩合反应。当反应在由醇和助溶剂组成的混合溶剂中进行时，得到了主要由环状二聚体meso-2组成的沉淀，表明沉淀驱动的非映对和区域选择性自组装过程。利用该体系作为沉淀诱导的基于可逆C-C键形成的自组装模型，我们全面研究了醇、助溶剂和底物烷基链长度对反应结果的影响。值得注意的是，乙氧基取代双醛1在甲醇/甲苯混合物中的反应有效地达到了平衡，产生了包含大环介介-2和甲苯的结晶沉淀，从中分离出介介-2的收率很高。

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Precipitation-Driven Diastereo- and Regioselective Macrocyclization via Benzoin Condensation: Effects of Solvents and Alkyl Chain Lengths

The benzoin condensation of a designed dialdehyde 1 with a terphenyl framework was investigated. When the reaction was carried out in mixed solvents composed of an alcohol and a co-solvent, a precipitate primarily consisting of the cyclic dimer meso-2 was obtained, indicating a precipitation-driven diastereo- and regioselective self-assembly process. Using this system as a model for precipitation-induced self-assembly based on reversible C-C bond formation, we comprehensively investigated the effects of the alcohol, co-solvent, and alkyl chain length of the substrate on the outcome of the reaction. Notably, the reaction of ethoxy-substituted dialdehyde 1 in MeOH/toluene mixture reached equilibrium efficiently, affording a crystalline precipitate incorporating macrocycle meso-2 and toluene, from which meso-2 was isolated in good yield.

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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.