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Hydride‐Donor Abilities of 1,4‐Dihydropyridines: A Comparison with π Nucleophiles and Borohydride Anions
Author(s) -
Richter Dorothea,
Mayr Herbert
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804263
Subject(s) - nucleophile , iminium , hydride , chemistry , borohydride , ion , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , hydrogen
How are dihydropyridines like indoles? Both groups of compounds have similar nucleophilicity parameters N and are therefore suitable substrates for iminium‐catalyzed reactions of α,β‐unsaturated aldehydes. The N parameters of 1,4‐dihydropyridines were derived from the rates of hydride transfer reactions to benzhydrylium ions (see scheme).