Mistry, Nisha;Fletcher, Stephen P. published 《Phosphoramidite ligands based on simple 1,2-diols: synthesis, use in copper-catalyzed asymmetric additions, and achirotopic stereogenic phosphorus centres》 in 2016. The article was appeared in 《Advanced Synthesis & Catalysis》. They have made some progress in their research.Name: rel-(1R,2S)-1,2-Diphenylethane-1,2-diol The article mentions the following:
Phosphoramidite ligands are widely used in catalysis and normally constructed from large C2-sym. diols such as BINOL or TADDOL. We report here on new ligands I (R1 = R2 = Ph , R1-R2 = (CH2)4; R3, R4 = CHMePh, CHPh2, iPr) based on a set of simple diols, 1,2-diphenyl-1,2-ethanediol, cis- and trans-1,2-cyclohexanol, that had been previously overlooked. Ligands based on (S,S)-trans-cyclohexanediol and (R,R)-(+)-1,2-diphenyl-1,2-ethanediol, in combination with both chiral and achiral amines, were tested in 3 different copper-catalyzed asym. reactions and up to 89% ee was observed A different ligand gave the best results in each reaction examined Using meso-cis-cyclohexanediol and meso-cis-diphenyl-1,2-ethanediol with a chiral non-racemic amine gave diastereomeric ligands bearing achirotopic stereogenic phosphorus atoms which were characterized with the assistance of x-ray crystallog. and variable temperature NMR studies. This work provides a new set of ligands that may be useful in some asym. reactions when phosphoramidites based on BINOL and TADDOL are ineffective. We also identify a novel stereochem. feature of phosphoramidites that may be useful in asym. catalysis and ligand design. To complete the study, the researchers used rel-(1R,2S)-1,2-Diphenylethane-1,2-diol (cas: 579-43-1) .
Desymmetrization of rel-(1R,2S)-1,2-Diphenylethane-1,2-diol(cas:579-43-1 Name: rel-(1R,2S)-1,2-Diphenylethane-1,2-diol) using chiral phosphine catalyst has been reported. Conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide has been reported.
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