Yb(
The syn-thioallylation of ynamides I (R = Ph, 4-methylphenyl, 3-cyanophenyl, etc.) to give products incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide was reported. The transformation is successful under ytterbium(III)-catalysis, providing access to highly substituted thioamino-skipped-dienes II (R1 = 2-propenyl, Ph, 2-fluorophenyl, naphthalen-2-yl, etc.) with broad substrate scope. Thus, tetrasubstituted olefins II (with four different functional groups: amide, Ph, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides I preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino diene III by ynamide I (Ar = Ph) syn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism. In the experiment, the researchers used many compounds, for example, 3-(Phenylethynyl)oxazolidin-2-one (cas: 888329-88-2Computed Properties of C11H9NO2).
3-(Phenylethynyl)oxazolidin-2-one (cas: 888329-88-2) belongs to oxazolidine derivatives. Oxazolidines are commonly obtained by reaction of strained heterocycles, mainly aziridines. Oxazolidines are cyclic condensation products of β-amino alcohols and aldehydes or ketone, and they undergo a facile and complete hydrolysis in aqueous solution. Alterations in carbonyl moiety control the rate of formation of a given β-amino alcohol. Oxazolidines are weaker bases (pKa 6–7) than parent β-amino alcohols and found to be more lipophilic than the parent compound at physiological pH.Computed Properties of C11H9NO2
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem