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

Lookup NU author(s): Dr Ross Harrington, Emeritus Professor Bill Clegg, Dr Michael Hall

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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.


Publication metadata

Author(s): Watson LJ, Harrington RW, Clegg W, Hall MJ

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2012

Volume: 10

Issue: 33

Pages: 6649-6655

Print publication date: 06/07/2012

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/C2OB26009C

DOI: 10.1039/C2OB26009C


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