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

Autori
Petković, Silvija

Vrsta, podvrsta i kategorija rada
Ocjenski radovi, diplomski rad, diplomski

Fakultet
Fakultet kemijskog inženjerstva i tehnologije

Mjesto
Zagreb

Datum
13.07

Godina
2015

Stranica
30

Mentor
Krištafor, Svjetlana

Neposredni voditelj
Ruzziconi, Renzo

Ključne riječi
organocatalysis; cinchona analogues; asymmetric induction; chirality

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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