4.6 Article

The Construction of Quaternary Stereocenters by the Henry Reaction: Circumventing the Usual Reactivity of Substituted Glyoxals

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 13, Pages 3768-3773

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002888

Keywords

asymmetric catalysis; copper; Henry reaction; N ligands; nucleophilic addition

Funding

  1. Ministerio de Ciencia e Innovacion
  2. FEDER [CTQ2006-14199, CTQ2009-13083]
  3. Generalitat Valenciana [ACOMP/2009/338]
  4. Universitat de Valencia

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The enantioselective Henry reaction between alkyl-and arylglyoxal hydrates and nitromethane catalyzed by Cu-II-iminopyridine complexes takes place regioselectively on the ketone carbonyl group to give chiral tertiary nitroaldols with high functional group density and enantiomeric excesses of up to 96%. Both aromatic and aliphatic glyoxals are suitable substrates for this reaction.

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