Synthesis of 伪,尾-Unsaturated Acylsilanes via Perrhenate-Catalyzed Meyer鈥揝chuster Rearrangement of 1-Silylalkyn-3-ols

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• 作者：Andrei Nikolaev ; Arturo Orellana
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 4, 2015
• 年：2015
• 卷：17
• 期：23
• 页码：5796-5799
• 全文大小：337K
• ISSN：1523-7052

文摘

We report the synthesis of 伪,尾-unsaturated acylsilanes via the perrhenate-catalyzed Meyer鈥揝chuster rearrangement of 1-silylalkyn-3-ols. Propargylic alcohols derived from TES-acetylene and substituted benzaldehydes can be converted to acylsilanes using a combination of p-TSA路H₂O and n-Bu₄N路ReO₄, or Ph₃SiOReO₃ in good yields. Some propargylic alcohols derived from ketones, as well as aliphatic and unsaturated aldehydes, can also be converted to acylsilanes; however, they were often prone to side reactions.