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A novel reaction for the functionalization of epoxy resins: New regio- and chemoselective ring-opening of epoxides with aryl silyl ether catalyzed by cesium fluoride

✍ Scribed by Yoko Nambu; Takeshi Endo


Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
238 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis


By use of cesium fluoride as a catalyst, aryl or alkyl glycidyl ethers were ring-opened by aryl trimethylsilyl ether to produce O-protected aryloxyhydrins with a quantitative regioselectivity for the first time. Alkyl silyl ether was ineffective for this ring-opening.

Hy the regioselective ring-opening of epoxides with trimethylsilyl aside', silyl halides2, silyl amides3, and silylated arylseleno14, various O-protected functionalized hydrins prospective as synthetic intermediates were obtained.