Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines was written by Wang, Gang;Franke, Jana;Ngo, Chinh Q.;Krische, Michael J.. And the article was included in Journal of the American Chemical Society in 2015.SDS of cas: 1122-71-0 This article mentions the following:
The chiral cyclometalated π-allyliridium ortho-C,O-benzoate complex derived from [Ir(cod)Cl]2, allyl acetate, 4-cyano-3-nitro-benzoic acid, and (R)-MeO-BIPHEP catalyzes the coupling of N-(p-nitrophenylsulfonyl) protected vinyl aziridine with primary alcs. to furnish branched products of C-C bond formation with good levels of anti-diastereo- and enantioselectivity. In the presence of 2-propanol, but under otherwise identical conditions, vinyl aziridine and aldehydes engage in reductive coupling to furnish an equivalent set of adducts with roughly equivalent levels of anti-diastereo- and enantioselectivity. Using enantiomeric iridium catalysts, vinyl aziridine reacts with unprotected chiral 1,3-diols in a site-selective manner to deliver the diastereomeric products of C-allylation syn- and anti-stereoisomers, resp., with good isolated yields and excellent levels of catalyst-directed diastereoselectivity. These adducts were directly converted to the diastereomeric 2,4,5-trisubstituted piperidines syn- and anti-stereoisomers. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0SDS of cas: 1122-71-0).
6-Methyl-2-pyridinemethanol (cas: 1122-71-0) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 1122-71-0
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts