Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles

  1. Lookup NU author(s)
  2. Dr Ross Harrington
  3. Emeritus Professor William Clegg
  4. Dr Michael Hall
Author(s)Watson LJ, Harrington RW, Clegg W, Hall MJ
Publication type Article
JournalOrganic & Biomolecular Chemistry
ISSN (print)1477-0520
ISSN (electronic)1477-0539
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The Diels-Alder cycloadducts of 4-vinylimidazoles and N-phenylmaleimide are shown to undergo facile intermolecular ene reactions. Overall the reaction of three simple molecules (a diene, a dienophile and an enophile) in a two-step process gives 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles with high yields, high atom economy and diastereocontrol of up to 5 new stereocentres.
PublisherRoyal Society of Chemistry
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