Rhodium-catalyzed Desymmetrization of non-annulated Azanorbornadienes and Azanorbornenes

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The project aims at the development of a rhodium-catalyzed desymmetrization of non-annulated azanorbornadienes and azanorbornenes. This novel method grants access to a variety of trans-substituted amino cyclohexadienes and cyclohexenes. Apart from widely used oxygen and nitrogen nucleophiles, carbon nucleophiles are to be tested in order to render aryl and alkyl substituted products accessible. With the use of difunctional nucleophiles, the synthesis of several chiral carbo and heterocycles is enabled, which are difficult to access to date. The structural motifs obtained are not only interesting for the synthesis of a variety of natural products, but are also part of widely used ligands for transition metal catalyzed reactions. Aside from the possibility of diversification of these ligands, the developed method enables the synthesis of chiral indolines, lactams or substituted amino cycloheptenes.