Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles.
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.
School of Chemistry, Newcastle University, Newcastle upon Tyne, UK.
Lynsey J
LJ
Watson
Ross W
RW
Harrington
William
W
Clegg
Michael J
MJ
Hall
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008301:Maleimides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D001562:Benzimidazoles; D007093:Imidazoles; D008301:Maleimides; C028525:N-phenylmaleimide; C425704:N-vinylimidazole