摘要
gHighly optically active 4-substituted-2(5H)-furanones 6a—6j were obtained in good yields with de≥98% by the tandem Michael addition/elimination reaction of chiral 3-bromo-2(5H)-furanone (4a), which was conveniently prepared starting from 2-furaldehyde under mild conditions. The products were identified on the basis of their sat-isfactory elemental analysis and spectroscopic data of IR, UV, 1H NMR, 13C NMR and mass spectra. The stereo-chemistry and absolute configuration of this type of compounds were established by the X-ray crystallographic study. The reaction provided a short and efficient synthesis of the interesting highly optically active 4-substituted-2(5H)-furanones containing an active pyrimidine and a purine base group.
gHighly optically active 4-substituted-2(5H)-furanones 6a—6j were obtained in good yields with de≥98% by the tandem Michael addition/elimination reaction of chiral 3-bromo-2(5H)-furanone (4a), which was conveniently prepared starting from 2-furaldehyde under mild conditions. The products were identified on the basis of their sat-isfactory elemental analysis and spectroscopic data of IR, UV, 1H NMR, 13C NMR and mass spectra. The stereo-chemistry and absolute configuration of this type of compounds were established by the X-ray crystallographic study. The reaction provided a short and efficient synthesis of the interesting highly optically active 4-substituted-2(5H)-furanones containing an active pyrimidine and a purine base group.
基金
Project supported by the National Natural Science Foundation of China (No. 29672004).
