Tr枚ger鈥檚 Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether

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• 作者：Josep Artacho ; Erhad Ascic ; Toni Rantanen ; Carl-Johan Wallentin ; Sami Dawaigher ; Karl-Erik Bergquist ; Michael Harmata ; Victor Snieckus ; Kenneth W盲rnmark
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：14
• 期：18
• 页码：4706-4709
• 全文大小：232K
• 年卷期：v.14,no.18(September 21, 2012)
• ISSN：1523-7052

文摘

Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tr枚ger鈥檚 base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.