engleski

Preparation of Chiral [2](5, 8)quinolinophane – Based Cinchonoid Analogue Organocatalysts for Stereoselective Syntheses

The aim of this thesis was to synthesize chiral cinchonoid analogues, [2](5, 8)quinolinophane and quinoline organocatalysts that could be used in stereoselective syntheses. The presence of the quinoline system makes the molecule of quinolinophane a great "building block" for the synthesis of chiral cinchona analogues as potential organocatalysts. In other words, it would be sufficient to introduce into the molecule a tertiary amino group and a chiral carbon bounded to a hydroxyl group to obtain a molecule that has all the elements of chirality as the natural cinchonoids. The only difference lies in the fact that a central chirality associated with quinuclidine ring of cinchonoids is replaced by the planar chirality associated with the system "quinolinophane". In addition, the quinolinophane constitutes a chiral "building block" of extreme versatility. In fact, through simple transformations, it is possible to obtain different structural combinations in which the determined elements for the asymmetric induction (the tertiary amino group, the hydroxylated chiral carbon and the planar chirality system) can be differently assembled. With that in mind, the scope was to determine contribution of planar and central chirality of (R)-[2]paracyclo[2](5, 8)quinolinophane derivatives exhibiting both type of chirality to the asymmetric induction (Figure 1). For sake of comparison envisaged was to prepare also some chiral (S)- and (R)-trifluoromethylsulfoxyamide derived from 4-bromoquinoline.

organocatalysis; cinchona analogues; asymmetric induction; chirality

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