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Project 10

Chiral auxiliaries based on tartaric acid. Synthesis and application in asymmetric synthesis

Supervisor: Prof. Michael Widhalm

Student: Tuvshinjargal Budragchaa

The subject of the present research project comprises a detailed investigation of synthetic routes to tailored chiral C4-entities accessible from natural tartaric acid, and their application in asymmetric transformations.
In the majority of published applications, the vicinal hydroxy groups of tartaric acid have been protected as cyclic ketal, while carboxylic groups have been converted into alcohols, amines, and phosphines etc. Particularly, TADDOLs and their analogues , bearing two adjacent diarylmethanol groups, have proven to be extremely versatile auxiliaries.

It is expected that the more controlled stereoinduction in asymmetric catalysis may be achieved through TADDOL analogues 1 with two different geminal aryl groups in α-positions i.e. introducing chiral center in close proximity to the metal center.

In order to reduce steric strain in catalytic intermediates the ligands will be further modified by replacing the cyclic ketal with benzyl/alkyl groups. Introducing an additional freely rotating σ-bond might facilitate the formation of chelates and/or improve the stability of transition states. On the other hand, a tuned electronic and steric interaction between α-aryl groups and substituents R3 (π-stacking in case of R3 = benzyl) will introduce an ordering principle and reduce the number of coexisting conformers of 2.

Subsequently, the new families of ligands will be tested for their efficiencies in catalytic benchmark reactions.

Initiativkolleg Functional Molecules
Währinger Str. 38
1090 Wien
T: +43 1 4277 70809
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