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Stable Axially Chiral Cyclohexylidenes from Catalytic Asymmetric Knoevenagel Condensation
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2024-05-07 , DOI: 10.1002/chem.202401243
Meijia Ying 1 , Kaixuan Wang 1 , Wenjun Yan 1 , Maoping Pu 1 , Lili Lin 2
Affiliation  

Axially chiral cycloalkylidenes are interesting but less developedaxially chiral molecules. Here, a bispidine‐based chiral amine catalytic system was developed to promote efficiently the asymmetric Knoevenagel condensation ofN‐protected oxindoles and benzofuranones with 4‐substituted cyclohexanones. A variety of alkylidenecycloalkanes with stable axial chirality were obtained in good yields with high er. Based on the absolute configuration determination of product and DFT calculations, a possible mechanism of stereoselective induction was proposed.

中文翻译:

催化不对称诺文格尔缩合反应生成稳定的轴向手性亚环己基

轴向手性亚环烷基是有趣的,但尚未开发的轴向手性分子。在此,开发了一种基于双吡啶的手性胺催化体系,以有效促进 N 保护的羟吲哚和苯并呋喃酮与 4-取代环己酮的不对称 Knoevenagel 缩合。多种具有稳定轴向手性的亚烷基环烷烃以良好的产率和较高的er得到。基于产物的绝对构型测定和DFT计算,提出了立体选择性诱导的可能机制。
更新日期:2024-05-07
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