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

✍ Scribed by Xue-E Fan; Min Huang; Hui Huang; Qing-Hua Chen

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 662 KB
• Volume: 22
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.20040221129

✦ Synopsis

Abstract

Highly optically active 4‐substituted‐2(5__H__)‐furanones 6a‐6j were obtained in good yields with de⩾98% by the tandem Michael addition/elimination reaction of chiral 3‐bromo‐2(5__H__)‐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, ^1^H 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(5__H__)‐furanones containing an active pyrimidine and a purine base group.