Diastereodivergent Carbometalation/Oxidation/Selective Ring Opening: Formation of All-Carbon Quaternary Stereogenic Centers in Acyclic Systems

Authors

  • Dr. Pierre-Olivier Delaye,

    1. The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
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  • Dr. Dorian Didier,

    1. The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
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  • Prof. Dr. Ilan Marek

    Corresponding author
    1. The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
    • The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel)
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  • This research was supported by the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (140/12). I.M. is holder of the Sir Michael and Lady Sobell Academic Chair.

Abstract

original image

A twofer: The title reaction sequence for cyclopropenes allows the preparation of aldehydes bearing α-quaternary stereocenters in a one pot-reaction from readily available starting materials. Through a diastereodivergent carbometalation reaction, both enantiomers of the corresponding aldehyde were obtained from the same cyclopropene derivative (see scheme).

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