MOLECULAR BELTS .2. SUBSTRATE-DIRECTED SYNTHESES OF BELT-TYPE AND CAGE-TYPE STRUCTURES

P R ASHTON, U GIRRESER, D GIUFFRIDA, F H KOHNKE, J P MATHIAS, F M RAYMO, A M Z SLAWIN, J F STODDART, D J WILLIAMS

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108 Citations (Scopus)

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
Pages (from-to)5422-5429
Number of pages8
JournalJournal of the American Chemical Society
Volume115
Issue number13
Publication statusPublished - 30 Jun 1993

Keywords

  • HOST GUEST COMPLEXATION
  • SUPRAMOLECULAR CHEMISTRY
  • CONTAINER COMPOUNDS
  • COLLARS
  • PERSPECTIVES
  • RECOGNITION
  • EQUIVALENTS
  • CAVITANDS
  • SOLVENTS
  • PROVIDE

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