o-Cyanobenzoate: A Recyclable and Reusable Stereo-directing Group for β-O-Glycosylation via Pd(0)-catalyzed Ferrier Rearrangement was written by Das, Pradip;Rahaman Molla, Mosidur;Kumar, Amit;Thakur, Rima. And the article was included in Chemistry – An Asian Journal in 2022.Reference of 2216-51-5 This article mentions the following:
Inner sphere Tsuji-Trost reaction has found recent application for β-selective Ferrier rearrangement of glycal substrates with alc. nucleophiles. Herein, we report an efficient and stereoselective synthesis of 2,3-dideoxy-β-O-glycosides from C3-(o-cyanobenzoate) ester protected glycal donors via Ferrier rearrangement under Pd(0)-catalyzed Tsuji-Trost conditions. The synthesized donors indeed reacted with a variety of acceptors to afford the corresponding glycosides in good yields and excellent β-stereoselectivity. The stereochem. outcome of the reactions has been found to be independent of the nature of protecting groups or conformational flexibility of the glycal donors. Furthermore, regeneration of ortho-cyanobenzoic acid post rearrangement makes it a recyclable and reusable stereo-directing group. A preliminary mechanistic study demonstrates the importance of cyano-group for the observed rearrangement and stereoselectivity. Incorporation of the directing group on the benzoate ester has altered the reactivity of the ester group as a leaving group for Tsuji-Trost as well as Ferrier Rearrangement pathway. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Reference of 2216-51-5).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Reference of 2216-51-5
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts