Lewis Acid Triggered Regioselective Magnesiation and Zincation of Uracils, Uridines, and Cytidines

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• 作者：Lydia Klier ; Eider Aranzamendi ; Dorothée Ziegler ; Johannes Nickel ; Konstantin Karaghiosoff ; Thomas Carell ; Paul Knochel
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 4, 2016
• 年：2016
• 卷：18
• 期：5
• 页码：1068-1071
• 全文大小：410K
• ISSN：1523-7052

文摘

The Lewis acid MgCl₂ allows control of the metalation regioselectivity of uracils and uridines. In the absence of the Lewis acid, metalation of uracil and uridine derivatives with TMPMgCl·LiCl occurs at the position C(5). In the presence of MgCl₂, zincation using TMP₂Zn·2LiCl·2MgCl₂ occurs at the position C(6). This metalation method provides easy access to functionalized uracils and uridines. Using TMP₂Zn·2LiCl·2MgCl₂ also allows to functionalize cytidine derivatives at the position C(6).