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

• 作 者: 范雪娥 黄敏 黄慧 陈庆华
• 机 构: Department of Chemistry, Luoyang Normal College,Department of Chemistry, Beijing Normal University,
• 出 处: Chinese Journal of Chemistry
• 发表日期: 2004年11期
• 关键词: Highly chiral heterocyclic bromo substituted spiro afford reagent elimination be

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) 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, 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.