Selective Rhodium- and Palladium-Catalyzed Hydroamination of Allenes with N-Containing Heterocycles and its Application in Total Synthesis

Beschreibung

N-allylic heterocycles are valuable building blocks in organic chemistry and their synthesis was intensively investigated in regard of chemo-, regio- and enantioselectivity. The main goal of this dissertation was the development of an intermolecular, atom-economic, rhodium-catalyzed hydroamination of allenes with various nitrogen-nucleophiles in an enantioselective manner. In a regiodivergent approach branched and linear allylated products were obtained in high selectivity. The synthetic applicability of the catalyzed asymmetric additions additionally demonstrated in the synthesis of Abacavir. Further projects of this work focused on the transition metal-catalyzed, selective hydroamination of terminal allenes with various nitrogen-containing heterocycles such as (benz)imidazoles, (benzo)triazoles and pyrazoles.

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Niels Thieme

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N-allylic heterocycles allenes rhodium-catalyzed hydroamination

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