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Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse Architectures

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  • This work was supported by the DFG (Emmy Noether Programm, SPP 1179 Organokatalyse). We thank Prof. Carsten Bolm for continued support and Chininfabrik Buchler GmbH, Braunschweig, for alkaloid samples.

Abstract

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Aminal pharm: Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.

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