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Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes

Author

Listed:
  • Yury Minko

    (The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel)

  • Morgane Pasco

    (The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel)

  • Lukas Lercher

    (The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel)

  • Mark Botoshansky

    (Laboratory for X-ray Analysis, Technion-Israel Institute of Technology, Haifa 32000, Israel)

  • Ilan Marek

    (The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel)

Abstract

The synthesis of an all-carbon quaternary stereocentre in an acyclic system is reported; the chemical transformation involves the formation of two new stereogenic centres—including the challenging all-carbon quaternary one in an aldol adduct—via a combined carbometalation–oxidation reaction, giving a stereodefined trisubstituted enolate.

Suggested Citation

  • Yury Minko & Morgane Pasco & Lukas Lercher & Mark Botoshansky & Ilan Marek, 2012. "Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes," Nature, Nature, vol. 490(7421), pages 522-526, October.
    • Handle: RePEc:nat:nature:v:490:y:2012:i:7421:d:10.1038_nature11569
    DOI: 10.1038/nature11569
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