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Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α‐C−H Bond Functionalization of Tertiary Amines

The challenging gold-catalyzed α-C−H bond functionalization of tertiary amine was achieved via the intermediacy of a reactive α-imino gold carbene. The use of a malonate group exerting electronic, steric and conformational synergistic effects was key to the success of the transformation. The tetrahydro-γ-carboline products could be subsequently oxidized to access structural motifs found in bioactive natural products.


Abstract

Direct C−H bond functionalization is a useful strategy for the straightforward formation of C−C and C−Heteroatom bonds. In the present work, a unique approach for the challenging electrophilic Au-catalyzed α-C−H bond functionalization of tertiary amines is presented. Electronic, steric and conformational synergistic effects exerted by the use of a malonate unit in the substrate were key to the success of this transformation. This new reactivity was applied to the synthesis of tetrahydro-γ-carboline products which, under oxidative conditions, could be converted into valuable structural motifs found in bioactive alkaloid natural products.

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