Dynamic Thermodynamic Resolution of Racemic 1,1′-Binaphthyl-2,2′-diol (BINOL)Click to copy article linkArticle link copied!
- Omer ShaashuaOmer ShaashuaDepartment of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 8410501, IsraelMore by Omer Shaashua
- Dennis PollokDennis PollokDepartment of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128 Mainz, GermanyMore by Dennis Pollok
- Alina DyadyukAlina DyadyukDepartment of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 8410501, IsraelMore by Alina Dyadyuk
- Alexander I. ShamesAlexander I. ShamesDepartment of Physics, Ben-Gurion University of the Negev, Beer-Sheva 8410501, IsraelMore by Alexander I. Shames
- Siegfried R. Waldvogel*Siegfried R. Waldvogel*[email protected]Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128 Mainz, GermanyMore by Siegfried R. Waldvogel
- Doron Pappo*Doron Pappo*[email protected]Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 8410501, IsraelMore by Doron Pappo
Abstract
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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