Application de la réaction de Wittig à la synthèse de dérivés de bromoénosuloses et d'esters bromoénuroniques. Note de laboratoire
✍ Scribed by Jean M. J. Tronchet; Olivier R. Martin; Jean-Bernard Zumwald
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- German
- Weight
- 237 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Use of the Wittig reaction for the synthesis of derivatives of bromoenosuloses and bromoenuronic esters
Treatment of 3‐O‐benzyl (or 3‐O‐methyl)‐1, 2‐O‐isopropylidene‐α‐D‐xylo‐pentodialdo‐1, 4‐furanoses (2 or 1) with acetylbromomethylidenetriphenylphosphorane (3), benzoylbromomethylidenetriphenylphosphorane (4) or bromoethoxycarbonylmethylidenetriphenylphosphorane (5) gave in good to excellent yields the expected enose (6‐‐11). In all cases but one (8 where some 10% of the E‐isomer was formed) the reaction led to the exclusive formation of the Z‐isomer whose configuration was established by NMR.
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