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A New Approach to Substituted Cyclobutanes: Direct β-Deprotonation/ Magnesiation of Cyclobutane Carboxamides

Philip Eaton, Mao‐Xi Zhang, Naruyoshi Komiya, Cai‐Guang Yang, Ian M. Steele, R. Gilardi

Open publisher page 23 citations

Abstract

BuMgN(i-Pr)2 is shown to be kinetically and thermodynamically efficient for deprotonation/magnesiation cis and β to an activating carboxamido group on a cyclobutane ring. The resulting carboxamido-stabilized amido-Grignards are useful reagents. The method provides an entirely new approach to controlled substitution on cyclobutanes. BuMgN(i-Pr)2 will also metalate pivaloyl amides.

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What this paper is about

BuMgN(i-Pr)2 is shown to be kinetically and thermodynamically efficient for deprotonation/magnesiation cis and β to an activating carboxamido group on a cyclobutane ring. The resulting carboxamido-stabilized amido-Grignards are useful reagents. The method provides an entirely new approach to controlled substitution on cyclobutanes. BuMgN(i-Pr)2 will also metalate pivaloyl amides.

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Available abstract

BuMgN(i-Pr)2 is shown to be kinetically and thermodynamically efficient for deprotonation/magnesiation cis and β to an activating carboxamido group on a cyclobutane ring. The resulting carboxamido-stabilized amido-Grignards are useful reagents. The method provides an entirely new approach to controlled substitution on cyclobutanes. BuMgN(i-Pr)2 will also metalate pivaloyl amides.

Key concepts: Cyclobutanes, Cyclobutane, Deprotonation, Chemistry, Ring (chemistry), Reagent, Stereochemistry, Medicinal chemistry

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