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Chemie und Stereochemie der Iridoide, XVII. Palladium‐katalysierte Substitution an Hexaacetylaucubin
Author(s) -
Weinges Klaus,
Ziegler Hans Jürgen
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101194
Subject(s) - chemistry , palladium , benzylamine , malonate , substitution reaction , piperidine , dimethyl malonate , allylic rearrangement , medicinal chemistry , nucleophile , hydride , nucleophilic substitution , catalysis , organic chemistry , hydrogen
Chemistry and Stereochemistry of Iridoids, XVII. – Palladium‐Catalysed Substitution of Hexaacetylacubin Acetoxy groups, in allylic position, can be replaced by nucleophiles in a palladium‐catalysed reaction. The reaction of hexaacetylaucubin ( 2 ) with piperidine or benzylamine regioselectively gives the crystalline, N‐containing iridoidglucosides 3 and 4 . With the anion of diemethyl malonate, 5 was obtained along with the byproduct 7 . Adding triethylammonium formate as a hydride donor, then the reaction gives 6 ; a reaction mechanism is discussed.