A Modular Synthesis of Multidentate S-, N- and O-Containing Meta- and Paracyclophanes

Research output: Contribution to journalArticle

  • Authors:
  • O. K. Rasheed
  • P. D. Bailey
  • A. Lawrence
  • P. Quayle
  • J. Raftery


The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine-​based macrocyclic compds. possessing multiple donor sites where chirality was readily introduced from (R)​-​alanine or (S)​-​alanine, a representative amino acid. A facile, regioselective, nucleophilic ring opening of aziridines by dithiols enabled the synthesis of thioether-​based linkers which on subsequent alkylation provided access to optically pure macrocycles. The synthesis of the target compds. was achieved by a reaction of (2S)​-​2-​methyl-​1-​[(4-​methylphenyl)​sulfonyl]​aziridine with 2,​2'-​(oxy)​bis[ethanethiol]​, 2,​2'-​[1,​2-​ethanediylbis(oxy)​]​bis[ethanethiol]​, 1,​3-​benzenedimethanethiol. The title compds. thus formed included 3,​17-​dithia-​6,​14,​23,​24-​tetraazatricyclo[,​12]​tetracosa-​1(23)​,​8,​10,​12(24)​,​19,​21-​hexaene derivs. and paracyclophane analogs.

Bibliographical metadata

Original languageEnglish
Pages (from-to)6988-6993
Number of pages5
JournalEuropean Journal of Organic Chemistry
StatePublished - 8 Oct 2015