Formula: C14H14O2In 2020, Murayama, Hiroaki;Heike, Yoshito;Higashida, Kosuke;Shimizu, Yohei;Yodsin, Nuttapon;Wongnongwa, Yutthana;Jungsuttiwong, Siriporn;Mori, Seiji;Sawamura, Masaya published 《Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp3-C-H Noncovalent Interactions》. 《Advanced Synthesis & Catalysis》published the findings. The article contains the following contents:
Iridium-catalyzed enantioselective transfer hydrogenation of ketones with formic acid was developed using a prolinol-phosphine chiral ligand. Cooperative action of the iridium atom and the ligand through alc.-alkoxide interconversion was crucial to facilitate the transfer hydrogenation. Various ketones including alkyl aryl ketones, ketoesters, and an aryl heteroaryl ketone were competent substrates. An attractive feature of this catalysis was efficient discrimination between the alkyl and aryl substituents of the ketones, promoting hydrogenation with the identical sense of enantioselection regardless of steric demand of the alkyl substituent and thus resulting in a rare case of highly enantioselective transfer hydrogenation of tert-alkyl aryl ketones. Quantum chem. calculations revealed that the sp3-C-H/π interaction between an sp3-C-H bond of the prolinol-phosphine ligand and the aryl substituent of the ketone was crucial for the enantioselection in combination with O-H···O/sp3-C-H···O two-point hydrogen-bonding between the chiral ligand and carbonyl group.rel-(1R,2S)-1,2-Diphenylethane-1,2-diol (cas: 579-43-1) were involved in the experimental procedure.
Desymmetrization of rel-(1R,2S)-1,2-Diphenylethane-1,2-diol(cas:579-43-1 Formula: C14H14O2) 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.
Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts