Hydride-donor abilities of 1,4-dihydropyridines: a comparison with pi nucleophiles and borohydride anions.
How are dihydropyridines like indoles? Both groups of compounds have similar nucleophilicity parameters N and are therefore suitable substrates for iminium-catalyzed reactions of alpha,beta-unsaturated aldehydes. The N parameters of 1,4-dihydropyridines were derived from the rates of hydride transfer reactions to benzhydrylium ions (see scheme).
Richter
Dorothea
D
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377 München, Germany.
Mayr
Herbert
H
D000447:Aldehydes / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D002384:Catalysis; D004095:Dihydropyridines / Q000737:chemistry*; D007700:Kinetics
D000447:Aldehydes; D000838:Anions; D001894:Borohydrides; D004095:Dihydropyridines