Catalytic Carbon Insertion into the 尾-Vinyl C鈥揌 Bond of Cyclic Enones with Alkyl Diazoacetates

详细信息    查看全文

• 作者：Sung Il Lee ; Byung Chul Kang ; Geum-Sook Hwang ; Do Hyun Ryu
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：15
• 期：7
• 页码：1428-1431
• 全文大小：256K
• 年卷期：v.15,no.7(April 5, 2013)
• ISSN：1523-7052

文摘

The first example of the boron Lewis acid catalyzed C_sp2鈥揌 functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF₃鈥t₂O or a newly designed oxazaborolidinium ion as a catalyst to afford 尾-functionalized cyclic enones from simple cyclic enones in a single step and high yields. The reaction mechanism was investigated with deuterium labeled 2-cyclohexen-1-one.