Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans was written by Xie, Youwei;Cheng, Gui-Juan;Lee, Sunggi;Kaib, Philip S. J.;Thiel, Walter;List, Benjamin. And the article was included in Journal of the American Chemical Society in 2016.Recommanded Product: (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol This article mentions the following:
We describe the design and development of the first catalytic asym. vinylogous Prins cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphorimidate (IDPi) catalyst is used. With a racemic dienyl alc., the reaction proceeds via a kinetic resolution DFT calculations suggest an explanation for unusually high stereoselectivity. In the experiment, the researchers used many compounds, for example, (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6Recommanded Product: (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol).
(S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Recommanded Product: (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts