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

摘要

Highly 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 satisfactory elemental analysis and spectroscopic data of IR, UV, ~1H NMR, ~(13)C NMR and mass spectra. The stereochemistry 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.