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Palladium(0)‐Catalyzed Alkynyl and Allenyl Iminium Ion Cyclizations Leading to 1,4‐Disubstituted 1,2,3,6‐Tetrahydropyridines
Author(s) -
Tsukamoto Hirokazu,
Kondo Yoshinori
Publication year - 2008
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.200800823
Subject(s) - iminium , reagent , alkyl , palladium , aryl , chemistry , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry
The biologically important title heterocyclic compounds can be synthesized by two methods based on the cyclization of alkynyl and allenyl iminium ions generated in situ in the presence of organometallic reagents (see scheme). Symmetrical and unsymmetrical tetrahydropyridines with diverse substituents R 4 were prepared in a single step under mild conditions. R 1 = n ‐, sec ‐, tert ‐alkyl; R 4 =aryl, 1‐alkenyl, alkyl, 1‐alkynyl, B(pinacolato).