Molecular Belts. 2. Substrate-Directed Syntheses of Belt-Type and Cage-Type Structures

Peter R. Ashton, Ulrich Girreser, Daniele Giuffrida, J. Fraser Stoddart, Franz H. Kohnke, John P. Mathias, Françisco M. Raymo, Alexandra M.Z. Slawin, David J. Williams, Franz H. Kohnke, Françisco M. Raymo, John P. Mathias

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

The trebly-diastereoselective synthesis and structural characterization of two macropolycyclic derivatives, which are based upon building blocks incorporating six-membered rings that are both [a,c]- and [a,d]-fused, have been achieved by a Diels-Alder oligomerization reaction sequence. The angular syn bisdienophile 3 has been used as a Diels-Alder building block with the bisdiene 12 in a trebly-diastereoselective synthesis of the angular macropolycyclic derivative 5. The incorporation of two diametrically-opposed [a,c]-fused units into the skeleton of 5 imposes a conical nature upon the cavity compared with the structures of macropolycyclic compounds such as the cyclacene derivatives 1 and 2. The construction of the angular macropolycyclic derivative 5 anticipates the use of the C3v trisdienophile 4, with the bisdiene 12, in the substrate-directed synthesis of a novel cage-like compound dubbed trinacrene 6. The structural characterization of both the angular macropolycyclic derivative 5 and trinacrene 6 has been achieved by high-field NMR spectroscopy and FABMS. In each case, the operation of treble diastereoselectivity during each cycloaddition step dictates the structures of the products, underlining the utility of these stereoregular Diels-Alder oligomerizations to control the formations of molecular structures.

Original languageEnglish (US)
Pages (from-to)5422-5429
Number of pages8
JournalJournal of the American Chemical Society
Volume115
Issue number13
DOIs
StatePublished - Jun 1 1993

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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