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Issue 33, 2012
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Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles

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Abstract

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.

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

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Publication details

The article was received on 23 May 2012, accepted on 05 Jul 2012 and first published on 06 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB26009C
Citation: Org. Biomol. Chem., 2012,10, 6649-6655
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    Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles

    L. J. Watson, R. W. Harrington, W. Clegg and M. J. Hall, Org. Biomol. Chem., 2012, 10, 6649
    DOI: 10.1039/C2OB26009C

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