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

Using CuI as a catalyst, N, N-diisopropylethylamine as ligand, n-butylamine as a base, and CHCN as solvent, the Glaser reaction of N-[5-( S)-alkoxy-2(5 H)-furanonyl] amino acid propargyl esters 1 at room temperature was investigated, and a series of new chiral 2(5 H)-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, H NMR, C NMR, MS, and elemental analysis. The brief synthesis of the series 2(5 H)-furanones derivatives with different functional units will afford not only an important synthetic strategy for the bioactive 2(5 H)-furanone derivatives as potential drug molecules but also a basis for the chiral polydiacetylene materials. [ABSTRACT FROM AUTHOR]