Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates

Article abstract of DOI:10.1016/S0040-4039(97)10199-X

N-methyl-2-oxazolidinones (4) are obtained stereo- and regio-selectively when 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates (1) are treated with concentrated sulfuric acid (1.0 equiv.) supported on silicagel in dichloromethane at 0 °C. 4 were shown to be intermediates for the construction of N-methylpyrrole ring. The structure and properties of 4 and related compounds are also described.