A Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles was written by Goncalves, Carlos R.;Lemmerer, Miran;Teskey, Christopher J.;Adler, Pauline;Kaiser, Daniel;Maryasin, Boris;Gonzalez, Leticia;Maulide, Nuno. And the article was included in Journal of the American Chemical Society in 2019.Formula: C12H20O6 This article mentions the following:
Functionalization at the α-position to carbonyl compounds has classically relied on enolate chem. As a result, generation of a new C-X bond whereby X is more electroneg. than carbon requires an oxidation event. By rendering the α-position of amides electrophilic through a mild and chemoselective Umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur and halogen nucleophiles can be used to generate α-functionalized amides. Over 60 examples are presented to establish the generality of this process and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodol. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Formula: C12H20O6).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Formula: C12H20O6
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem