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 and Biomolecular Chemistry
Year2012
Volume10
Issue33
Pages6649-6655
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
URLhttp://dx.doi.org/10.1039/C2OB26009C
DOI10.1039/C2OB26009C
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