An Efficient Synthesis of Highly Optically Active 4-Substituted- 2(5H)-furanones from Chiral 3-Bromo-2(5H)-furanone  

作　　者：范雪娥 黄敏 黄慧 陈庆华 

机构地区：[1]Department of Chemistry, Luoyang Normal College [2]Department of Chemistry, Beijing Normal University, Beijing 100875, China

出　　处：《Chinese Journal of Chemistry》2004年第11期1359-1365,共7页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China (No. 29672004).

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.

关 键 词：optically active 4-substituted-2(5H)-furanone tandem asymmetric Michael addition/elimination re-action pyrimidine or purine base group X-ray crystallography 

分 类 号：O621[理学—有机化学]