New cyclic chiral pseudo-peptides as organocatalysts

ORGN 763

Izaskun Gutiérrez Landa, izaskun@web.de and Gebhard Haberhauer, gebhard.haberhauer@urz.uni-heidelberg.de. Department of Organic Chemistry, University of Heidelberg (Germany), AK Haberhauer, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
The last few years have witnessed a spectacular advancement in new catalytic methods based on metal-free organic molecules. In many cases, these small compounds give rise to extremely high enantioselectivitys. Chiral amines play a main role in this expanding area. Recent studies have shown that organic catalysts bearing chiral cyclic amines such as proline-derived compounds and modified chinchona alkaloids are promising catalysts. We describe the synthesis of new pseudo-peptidic chiral platforms as organocatalysts which are derived from natural amino acids. The presence of three five-membered heteroaromatic rings leads to a rigid scaffold. Different functional groups (R1-4) are introduced to tune the catalytic activity of the platform. We expect to catalyze enantioselectively reactions using these platforms as chiral Lewis-base/nucleophilic catalysts. In studies, we carried out on the 1,4-addition of thiols to cyclic enones, organic asymmetric catalysis by our compounds was observed. Recently we have been working on the development of new pseudo-peptidic platform-catalyzed enantioselective reactions.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005