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Chiral Concave 1,10-Phenanthrolines for Enantioselective Catalysis
Lisa Reck, Ulrich Lüning*
Otto-Diels-Institut für Organische Chemie, Olshausenstr. 40, 24098 Kiel, GER
lreck@oc.uni-kiel.de, luening@oc.uni-kiel.de
In the development of new catalysts for asymmetric synthesis, enzymes are often used
as a model. The three-dimensional concave environment of the active centre is
responsible for the high selectivity. Against this background, concave macrocyclic,
mostly bimacrocyclic, compounds have been developed which can be compared to a
“lampshade” with the concave environment as the “shade” and the active centre as the
“light bulb”. [1] Structurally, these concave reagents are much less demanding than
enzymes but they are also much more stable concerning different influences like pH or
temperature.
One group of concave reagents are the concave 1,10-phenanthrolines whose achiral
variants were successfully used for diastereoselective metal catalysis. [2,3] To enable
enantioselective catalysis, it is necessary to build a chiral cavity which can be realized
by the use of naphthyl units.
O
O
N
X
A
N
O
O
O
O
N N
X
B
O
O
X=(CH 2) n
Figure 1: Achiral concave 1,10-phenanthroline (A), axially chiral concave 1,10-phenanthroline (B).
This contribution will show the synthetic procedure to obtain chiral concave 1,10phenanthrolines
as well as possible separation techniques for the enantiomers which are
the prerequisites for their final usage as enantioselective catalysts.
1 U. H. Brinker, J.-L. Mieusset, Molecular Encapsulation, John Wiley & Sons 2010, 175-199.
2 F. Löffler, M. Hagen, U. Lüning, Synlett. 1999, 1826-1828.
3 M. Gelbert, U. Lüning, Supramol. Chem. 2001, 12, 435-444.