Ethanol as a Hydrogenating Agent: Palladium-Catalyzed Stereoselective Hydrogenation of Ynamides to Give Enamides was written by Siva Reddy, Alla;Kumara Swamy, K. C.. And the article was included in Angewandte Chemie, International Edition in 2017.Name: 3-(Phenylethynyl)oxazolidin-2-one This article mentions the following:
Ethanol is shown to act as a hydrogenating agent for ynamides R1CCNHR2R3 [R1 = cyclopropyl, Ph; R2 = Me, Ph, PhCH2, 2-O2NC6H4CH2, R3 = 4-MeC6H4SO2; R2 = Me, R3 = 4-MeOC6H4SO2, 2-thienylsulfonyl, (PhO)2P(O), etc.; R2R3 = o-CH2C6H4SO2; etc.] under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction showed stereoselectivity for E-enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source gave Z-enamides. The role of ethanol in this transfer hydrogenation was demonstrated in deuterium labeling experiment In the experiment, the researchers used many compounds, for example, 3-(Phenylethynyl)oxazolidin-2-one (cas: 888329-88-2Name: 3-(Phenylethynyl)oxazolidin-2-one).
3-(Phenylethynyl)oxazolidin-2-one (cas: 888329-88-2) belongs to oxazolidine derivatives. Oxazolidine-based compounds are well-known chiral auxiliaries and strategic molecular moieties in chemistry since they can effectively mask or mimic amino acid units or amino alcohols. Oxazolidines are commonly used as metal ligands in asymmetric catalysis, synthetic intermediates in organic synthesis, and also used as the protecting groups.Name: 3-(Phenylethynyl)oxazolidin-2-one
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem