A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tr枚ger鈥檚 Base

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• 作者：Sami Dawaigher ; Kristoffer M氓nsson ; Erhad Ascic ; Josep Artacho ; Roger M氓rtensson ; Nagarajan Loganathan ; Ola F. Wendt ; Michael Harmata ; Victor Snieckus ; Kenneth W盲rnmark
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：80
• 期：24
• 页码：12006-12014
• 全文大小：447K
• ISSN：1520-6904

文摘

An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tr枚ger鈥檚 base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tr枚ger鈥檚 base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tr枚ger鈥檚 base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.