An efficient synthesis of highly optically active 4‐substituted‐2(5H)‐furanones from chiral 3‐bromo‐2(5H)‐furanone

Abstract

AbstractHighly 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, W, 1H NMR, 13C 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.