Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings
✍ Scribed by Fu-Ling Xue, Jian-Xiao Li, Zhao-Yang Wang…
- Book ID
- 120765665
- Publisher
- Springer Netherlands
- Year
- 2012
- Tongue
- English
- Weight
- 695 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0922-6168
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📜 SIMILAR VOLUMES
## 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.
Easily available 3,4-dibromo-2(5H)-furanone undergoes a regioselective cross-coupling reaction with alkylboronic acids in the presence of catalytic amounts of PdCl2(MeCN)2 and AsPh3 and a large molar excess of Ag2O to provide the corresponding 4-alkyl-3-bromo-2(5H)-furanones in satisfactory yields.