4.4 Article

An 'impossible' macrocyclisation using conformation directing protecting groups

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 19, Pages 2236-2238

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.02.186

Keywords

Macrocycles; Foldamers; Supramolecular chemistry; Protecting groups

Funding

  1. University of Leeds
  2. Engineering and Physical Sciences Research Council [EP/D077842/1]
  3. EPSRC [EP/D077842/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/D077842/1] Funding Source: researchfish

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A p-benzenetricarboxamide macrocycle linked through secondary cis amides is obtained via cyclisation and subsequent deprotection of a folded linear precursor. Secondary benzamides strongly prefer the trans conformation, therefore this synthesis can be considered 'impossible' without recourse to protecting groups. (C) 2009 Elsevier Ltd. All rights reserved.

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