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Bioconjugates of Enantiomerically Pure Organopalladium Compounds by Metal‐Assisted Positional Selective Transesterifications at Palladium Enolates
Author(s) -
Hashmi A. Stephen K.,
Riedel Dominic,
Grundl Marc A.,
Wittel Bärbel C.,
Föll Andreas,
Lubkoll Jana,
Traut Telisha,
Hewer Raymond,
Rominger Frank,
Frey Wolfgang,
Bats Jan W.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003308
Subject(s) - organopalladium , palladium , sonogashira coupling , chemistry , combinatorial chemistry , nucleophile , group 2 organometallic chemistry , transesterification , organic chemistry , catalysis , molecule
The synthesis of enantiomerically pure palladatricyclo[4.1.0.0 2,4 ]heptanes and their modification by an unprecedented and very efficient positional selective transesterification is described. The mild reaction conditions are most probably based on an acceleration of the transesterification due to assistance by the metal. This novel approach allows straightforward access to a large number of structurally diverse organometallic complexes. The functional groups on the newly installed ester moieties were modified by using standard peptide synthesis protocols, Sonogashira reactions, and nucleophilic substitution reactions. The cellular uptake of these organometallic species was traced by confocal microscopy and their biological activity was evaluated by using different cell lines. Inhibition of cell growth and induction of apoptotic cell death by these novel palladium heterocycles are equivalent to Cisplatin.