Synthesis of chiral 2(5H)-furanone derivatives with 1,3-butadiyne structure

Using CuI as a catalyst, N,N-diisopropylethylamine as ligand, n-butylamine as a base, and CH3CN as solvent, the Glaser reaction of N-[5-(S)-alkoxy-2(5H)-furanonyl] amino acid propargyl esters 1 at room temperature was investigated, and a series of new chiral 2(5H)-furanone derivatives containing 1,3-butadiyne structure have been synthesized as designed, with yields of 49–84 % (mostly over 66 %). Sixteen target molecules 2 were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis. The brief synthesis of the series 2(5H)-furanones derivatives with different functional units will afford not only an important synthetic strategy for the bioactive 2(5H)-furanone derivatives as potential drug molecules but also a basis for the chiral polydiacetylene materials.