Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization

H W Lam, G J Murray, J D Firth, Hon Lam

Research output: Contribution to journalArticlepeer-review

Abstract

4-Hydroxypiperidin-2-ories may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of alpha,beta-unsaturated amides with ketones. Used in combination with proline-catalyzed asymmetric Mannich reactions, this methodology enables the enantioselective synthesis of more highly functionalized piperidin-2-ones and hydroxylated piperidines.

Original languageEnglish
Pages (from-to)5743-5746
Number of pages4
JournalOrganic letters
Volume7
Issue number25
DOIs
Publication statusPublished - 8 Dec 2005

Keywords

  • 3-COMPONENT MANNICH REACTION
  • ENANTIOSELECTIVE SYNTHESIS
  • ASYMMETRIC-SYNTHESIS
  • STRYKERS REAGENT
  • ENONES
  • HYDROGENATION
  • CONSTRUCTION
  • PIPERIDINES
  • GENERATION
  • NITROGEN

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