Abstract
A terminal alkyne was prepared, which is linked by a carbon-carbon
bond to a conformationally restricted, U-shaped chiral lactam, that
is, more precisely, to carbon atom C7 of 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one.
The alkyne was connected to various ligands (bipyridine, terpyridine,
pybox) by Sonogashira cross-coupling with the respective bromides
or triflates. The resulting products were converted into four defined
ruthenium complexes (58-94% yield). The complexes
contain a catalytically active metal center, which is spatially
remote from the hydrogen-bonding motif of the chiral lactam. Preliminary
experiments with one of these complexes proved that the complex
shows catalytic activity in oxidation reactions and that enantioselectivity
is achieved due to substrate coordination to the chiral lactam.
Key words
supramolecular chemistry - hydrogen bonds - catalysis - coordination chemistry - cross-coupling
reactions
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