Mild and selective reduction of imines: formation of an unsymmetrical macrocycle.
During investigations of 5, a [3 + 3] Schiff-base macrocycle with six imines, a partially reduced Schiff-base macrocycle, 6, possessing one CH(2)NH and five imine groups was obtained. Control experiments and deuterium labeling indicate that the macrocycle is reduced by a benzimidazoline generated during the reaction. Benzimidazolines may be convenient reagents for the mild and selective reduction of imines.
Gallant
Amanda J
AJ
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
Patrick
Brian O
BO
MacLachlan
Mark J
MJ
D003500:Cyclization; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction
D007097:Imines