A versatile preparation of a-alkoxyphosphonium bromides leading to en01 ethers by Wittig coupling was exploited for the convergent synthesis of pheromones from the Douglas-fir tussock moth and the olive fly Dacus oleae as well as an oxaspirolactone and C-glycoside.
Preparation of dimethylsilyl bis-enol ethers
✍ Scribed by Zacharia A. Fataftah; Mustafa R. Ibrahim; Mahmoud S. Abu-Agil
- Book ID
- 104218992
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 222 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Dichlorodimethylsilane is reacted with two equivalents of ketone enolates to give dimethylsilyl bis-enol ethers in good yields. Lithium tetramethylpiperidide (Li?Mp) as well as triethylamine (TEA) are used in deprotonation of ketones. An intramolecular aldol type of coupling has been achieved in an excellent yield on treatment of the dimethylsilyl bis-enol ether, derived from cyclohexanone, with TiClll.
📜 SIMILAR VOLUMES
Treatment of enol silyl ethers with the mild nitrating agent tetranitromethane gives good yields of unitroketones at room temperature and below.