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

Yury Minko, Morgane Pasco, Lukas Lercher, Mark Botoshansky and Ilan Marek ()
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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

Nature, 2012, vol. 490, issue 7421, 522-526

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.

Date: 2012
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DOI: 10.1038/nature11569

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