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Deamination of the Amino Acid Fragment in Imine Metallacycles: Unexpected Synthesis of an NH‐Aldimine Organometallic Compound
Author(s) -
Albert Joan,
Cadena J. Magali,
González Asensio,
Granell Jaume,
Solans Xavier,
FontBardia Mercè
Publication year - 2006
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.200500099
Subject(s) - aldimine , chemistry , imine , deamination , triphenylphosphine , medicinal chemistry , pyridine , stereochemistry , lewis acids and bases , organic chemistry , catalysis , enzyme
We report that the action of Lewis bases, such as triphenylphosphine, pyridine, or trimethylamine, on imine metallacycles derived from amino acids leads to the formation of the first organometallic compound of an NH aldimine, a highly reactive organic species, and the corresponding α‐ketoester, in a deamination reaction that mimics the metabolism of α‐amino acids. The synthesis of different cyclopalladated compounds by a reaction between palladium acetate and the Schiff bases 2,4,6‐Me 3 C 6 H 2 CHNCH(R 1 )COOR 2 (R 1 =CH 2 Ph, R 2 =Et and R 1 =Ph, R 2 =Me) is also reported.