Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether

Summary, in English

Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's 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.

• Author: Josep Artacho Ruiz; Erhad Ascic; Toni Rantanen; Carl-Johan Wallentin; Sami Dawaigher; Karl-Erik Bergquist; Michael Harmata; Victor Snieckus; Kenneth Wärnmark
• Department/s: Department of Chemistry; Centre for Analysis and Synthesis
• Publishing year: 2012
• Language: English
• Pages: 4706-4709
• Publication/Series: Organic Letters
• Volume: 14
• Issue: 18
• Links: http://dx.doi.org/10.1021/ol302022y
• Document type: Journal article
• Publisher: The American Chemical Society (ACS)
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1523-7052