化学
乙腈
加合物
二醇
溴化物
对映体
产量(工程)
分辨率(逻辑)
催化作用
药物化学
氧化还原
动力学分辨率
有机化学
对映选择合成
热力学
计算机科学
人工智能
物理
作者
Omer Shaashua,Dennis Pollok,Alina Dyadyuk,Alexander I. Shames,Siegfried R. Waldvogel,Doron Pappo
出处
期刊:Organic Letters
[American Chemical Society]
日期:2024-03-06
卷期号:26 (10): 2129-2134
被引量:1
标识
DOI:10.1021/acs.orglett.4c00520
摘要
A dynamic thermodynamic resolution method for converting (R/S)-BINOL (1,1′-binaphthyl-2,2′-diol) into (R)-BINOL in 100% theoretical yield is reported. This technique involves mixing (R/S)-BINOL with N-benzyl cinchonidinium bromide (1 equiv) and a [Cu2(tmeda)2(μ-OH)2]Br2 (2.5 mol %) redox catalyst in acetonitrile. In the background of this process is the observation that the energy for atropoisomerization decreases significantly when an electron is removed from BINOL. Therefore, it is possible to convert both enantiomers into the thermodynamically favorable [N-benzyl cinchonidinium bromide·(R)-BINOL] adduct.
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