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

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Abstract

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.

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  • Organic Chemistry
Original languageEnglish
Pages (from-to)4706-4709
JournalOrganic Letters
Volume14
Issue number18
Publication statusPublished - 2012
Publication categoryResearch
Peer-reviewedYes