272772-57-3

Upstream product

• 199926-83-5 ethyl (R)-(+)-6-(N-tert-butoxycarbonyl)amino-3-ethoxy-7-phenylhepta-2,4-dienoate 
• 145822-68-0 (E)-[2-ethoxy-3-(ethoxycarbonyl)-2-propenylidene]triphenylphosphorane 
• 199926-97-1 ethyl (R)-(+)-6-(N-tert-butoxycarbonyl-N-methyl)amino-3-ethoxy-7-phenylhepta-2,4-dienoate 
• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 

Downstream Products

• 199927-14-5 (4R,5R)-(+)-5-(3-ethoxycarbonyl-2-oxo)propyl-3-(N-methyl)-4-benzyl-2-oxazolidinone 

Relevant academic research and scientific papers

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

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.

Synthesis and reaction of chiral 4,5-disubstituted 2-oxazolidinones from 3-ethoxy-6-(N-alkyl-N-tert-butoxy- carbonyl)aminohexa-2,4-dienoates in the presence of concentrated sulfuric acid supported on silica gel

Reaction of chiral 3-ethoxy-6-(N-alkyl-N-tert-butoxycarbonyl)amino-hexa- 2,4-dienoates (3) and related compounds with 97% concentrated sulfuric acid supported on silica gel proceeded stereo- and regio-selectively to yield chiral 4,5-disubstituted N-alkyl-2-oxazolidinones (7). Under the limited conditions, 7 were converted into N-alkyl-2-pyrrolylacetates (8) and 2- oxazolidinone derivatives (12) which may serve as a chiral auxiliary.