Vinylogous Mukaiyama鈥揗ichael Reactions of Dihydropyridinones

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• 作者：Hui Li ; Jimmy Wu
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5424-5427
• 全文大小：416K
• ISSN：1523-7052

文摘

An In(III)-catalyzed vinylogous addition of O-silyl vinylketene acetals to 2,3-dihydro-4-pyridinones has been developed. The method features the unprecedented employment of supersilyl groups to influence the 纬 versus 伪 regiochemical control of vinylogous Mukaiyama鈥揗ichael (vM鈭扢ichael) reactions when 纬-substituted O-silyl vinylketene acetals are used. We also demonstrate that these reactions allow facile access to quinolizidine-based alkaloids such as deoxynupharidine and well as lasubine I and II.