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DOMINOCAT Report Summary

Project ID: 320493
Funded under: FP7-IDEAS-ERC
Country: Germany

Final Report Summary - DOMINOCAT (Asymmetric Organodomino Catalysis)

It has always been the dream of chemists to imitate Nature’s enzyme catalyzed machinery in the selective synthesis of complex molecules under mild conditions in the compartment of a living cell. While Nature needed billions of years to reach such a level of elegance and synthetic efficiency, chemists have only had less than two hundred years to develop synthetic methodologies in the laboratory. As of today the best method to mimic Nature is asymmetric catalysis. While bio- and metal-catalysis have been developed in the last fifty years to an already a high level of efficiency, it has only been since around the turn of the millennium that a third pillar of catalysis appeared, namely organocatalysis, the catalysis with small organic molecules.
Within the realm of organocatalysis asymmetric organocatalytic domino reactions, the topic of our ERC Advanced Grant project “DOMINOCAT”, turned out to be an attractive research area allowing to fulfill the modern criteria of “green chemistry” and sustainability. The goal was to selectively catalyze several consecutive reactions in a single vessel (like falling domino stones) leading to complex biologically relevant molecules.
The period of the grant turned out to be very successful and progressed mainly as originally planned. Quite a number of new efficient and highly selective simple, triple and quadruple domino reactions have been developed (two, three or four sequential reactions in one pot), thereby significantly advancing the strategic arsenal of synthetic chemistry. Polysubstituted carbo- and heterocycles could be obtained selectively in this way bearing up to six stereocenters. By employing special organocatalysts, which are able to activate molecules through hydrogen bonds (squaramides), the catalyst loading could be dramatically lowered (<0,2 mol%). In addition, we demonstrated that the novel organocatalytic domino protocols are scalable to at least gram amounts of final products allowing screening tests for a potential bioactivity and future industrial applications.
In the course of the ERC grant, a 2,5 day symposium “DOMINOCAT 1” was held at Aachen with more than 150 participants and 28 lectures presented by the leading scientists in the field from 16 different countries around the world. It offered the unique chance for the professors and young coworkers to discuss the state of the art of organodomino catalysis and the related chemistry around it.
In the course of the project beside of the simple, triple and quadruple cascades, the high hurdle of quintuple domino reactions was attempted. Unfortunately we had not been able to reach this goal.
In addition, the merger of gold/silver catalysis with organocatalysis was successfully investigated as well as mechanistic studies using mass spectrometric measurements in cooperation with Dr. Schrader, MPI Mülheim and computational calculations in cooperation with Prof. F. Schoenebeck in our institute.

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