• Medientyp: E-Artikel
  • Titel: One‐Pot Quinine‐Catalyzed Synthesis of α‐Chiral γ‐Keto Esters: Enantioenriched Precursors of cis‐α,γ‐Substituted‐γ‐Butyrolactones
  • Beteiligte: Meninno, Sara; Volpe, Chiara; Lattanzi, Alessandra
  • Erschienen: Wiley, 2016
  • Erschienen in: Advanced Synthesis & Catalysis
  • Sprache: Englisch
  • DOI: 10.1002/adsc.201600427
  • ISSN: 1615-4150; 1615-4169
  • Schlagwörter: General Chemistry
  • Entstehung:
  • Anmerkungen:
  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>A highly enantioselective one‐pot synthesis of important building blocks, α‐chiral γ‐keto esters, has been developed by combining a quinine‐catalyzed Michael addition of malononitrile to <jats:italic>trans</jats:italic>‐enones followed by magnesium monoperoxyphthalate (MMPP) oxidation. These synthons proved to be useful reagents for a simple access to challenging <jats:italic>cis</jats:italic>‐α,γ‐disubstituted γ‐butyrolactones in good diastereoselectivity and high enantiocontrol.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/png" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/adsc201600427-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text> </jats:p>