Synthesis of Multisubstituted Cyclohexenes and Cyclopentenes via Cascade Michael/Aldol/Annulative SuFEx/β-Sultone Desulfonation of β-Arylethenesulfonyl Fluorides

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-07-25 DOI:10.1039/d5qo00837a

Fang Zhang, Qichao Zhang, Pei Xie, Qifan Wang, Lin He, Zhihua Cai, Guangfen Du

引用次数: 0

Abstract

The first β-sultone desulfonation facilitated diastereoselective synthesis of functional cyclohexenes and cyclopentenes is described. Under the mediation of Cs2CO3, γ-ketomalononitriles reacted with β-arylethenesulfonyl fluorides through a cascade Michael addition/aldol reaction/annulative SuFEx click reaction/β-sultone desulfonation process to afford functionalized cyclohexenes in 40-99% yields and excellent cis-selectivity. In addition, β-ketomalononitriles undergo similar cascade reaction with β-arylethenesulfonyl fluorides to produce functional cyclopentenes in 57-99% yields with excellent trans-selectivity. A possible mechanism was proposed based on control experiments and DFT calculations.

查看原文本刊更多论文

β-芳基磺酰氟级联Michael/Aldol/环结SuFEx/β-磺酮脱硫合成多取代环己烯和环戊烯

介绍了β-磺酸酮第一次脱硫催化功能环己烯和环戊烯的非对映选择性合成。在Cs2CO3的催化作用下，γ-酮腈与β-芳基磺酰氟化合物通过Michael加成/醛醇反应/环结SuFEx键合反应/β-磺酮脱硫反应，得到了40-99%收率的功能化环己烯，并具有良好的顺式选择性。此外，β-酮酮腈与β-芳基磺酰氟发生类似的级联反应，产率为57-99%，具有优异的反式选择性。基于控制实验和DFT计算，提出了一种可能的机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.