172879-74-2Relevant articles and documents
Synthesis of (S)-3,4-Dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-Oxide
March, Pedro de,Figueredo, Marta,Font, Josep,Gallagher, Timothy,Milan, Sergio
, p. 2097 - 2098 (1995)
The synthesis of a series of new enantiopure 3,4-dihydro-2H-pyrrole derivatives including the title nitrone and its cycloaddition product to dimethyl acetylenedicarboxylate is described.
An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones
Xia, Qian,Ganem, Bruce
, p. 1597 - 1598 (2007/10/03)
Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Δ1-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported.
Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide
Busque, Felix,De March, Pedro,Figueredo, Marta,Font, Josep,Gallagher, Timothy,Milan, Sergio
, p. 437 - 445 (2007/10/03)
A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate.
