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Synlett 1998; 1998(12): 1381-1383
DOI: 10.1055/s-1998-1968
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Traceless Linkers for Solid-phase Synthesis. Homo- and Hetero-Diels-Alder Reactions of o-Quinodimethanes

Donald Craig* , Michael J. Robson, Simon J. Shaw
  • *Centre for Chemical Synthesis, Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.; Fax + 44 171-594 5804; E-mail: dcraig@ic.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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The synthesis and Diels-Alder reactions of a polymer-supported o-quinodimethane are described. Reaction with dimethyl acetylenedicarboxylate, benzoquinone and trichloroacetonitrile as dienophiles gives respectively substituted naphthalenes or an isoquinoline off-resin, whilst reaction with aldehydes and imines gives polymer-supported benzodihydropyrans and tetrahydroisoquinolines. The latter heterocyclic products undergo Lewis or Brønsted acid-mediated cleavage reactions which allow incorporation of further functionality at the point of cleavage whilst leaving no trace of attachment to the polymer support.

solid-phase synthesis - Diels-Alder - o-quinodimethane - traceless linker