Thermal 1,3-trityl migrations in Diels-Alder domino reactions of 1-trityl-4-vinyl-1H-imidazoles.
Under thermal conditions, tritylimidazoles have been shown to undergo sterically driven N-->N trityl migrations, in disagreement with previously published reports. These migrations are a key step in several highly diastereoselective domino reaction sequences (Diels-Alder, [1,3]-H shift, [1,3]-trityl migration and Diels-Alder, [1,3]-H shift, [1,3]-trityl migration, Michael reaction) leading to architecturally complex molecules.
Cotterill
Lynsey J
LJ
School of Chemistry, Newcastle University, Newcastle upon Tyne NE1 7RU, UK.
Harrington
Ross W
RW
Clegg
William
W
Hall
Michael J
MJ
D003500:Cyclization; D007093:Imidazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013696:Temperature; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
D007093:Imidazoles; D014320:Triphenylmethyl Compounds