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One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases

Authors


  • We thank Dr. D. Jeannerat and A. Pinto for NMR measurements, the University of Geneva, and the Swiss National Science Foundation for financial support. We also acknowledge the contributions of the Sciences Mass Spectrometry (SMS) platform at the Faculty of Sciences (University of Geneva), and the CRCMM and the Spectropole at the University of Aix-Marseille for computer time and use of the VCD facility, respectively.

Abstract

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Bridging the gap: Configurationally stable ethano-bridged Tröger bases have been prepared in a single step by the direct rhodium(II)-catalyzed reaction of methano-bridged Tröger bases and diazo esters (see scheme). The process is general, enantiospecific, diastereoselective (with introduction of a new quaternary carbon center), and regioselective.

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