Stereoselectivity in the synthesis of polyacene derivatives by repetitive Diels-Alder reactions

Peter R. Ashton*, George R. Brown, Diane R. Smith, J. Fraser Stoddart, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The bisaryne generated from 1,4,5,8-tetramethyl- 2,3,6,7-tetrabromonaphthalene reacts with 2,5-dymethylfuran to give - through the intermediacy of the 1:1 adduct 1 - the 2:1 adducts 2, with the major isomer 2a, the one with the anti-configuration as revealed by X-ray crystallography and rationalised by molecular mechanics. Diels-Alder reactions of the anti-bisdienophile 2a with 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane proceed with complete treble diastereoselectivity to give only one 1:1 adduct 3 and a single 2:1 adduct 4.

Original languageEnglish (US)
Pages (from-to)8337-8340
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number51
DOIs
StatePublished - Dec 17 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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