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Highly stereoselective synthesis of spiropyrazolones

  • Andrea Nekane R. Alba
  • , Alex Zea
  • , Guillem Valero
  • , Teresa Calbet
  • , Merce Font-Bardía
  • , Andrea Mazzanti
  • , Albert Moyano
  • , Ramon Rios
  • Universitat de Barcelona
  • University of Bologna

Research output: Contribution to journalArticlepeer-review

119 Scopus citations

Abstract

The synthesis of spiro compounds through a Michael-Michael-aldol reaction is reported. The reaction affords spiropyrazolone derivatives in good yields, in almost diastereo- and enantiopure form, and is catalyzed by diphenylprolinol derivatives. The reaction showed strong nonlinear effects. Remarkably, when a catalyst with 70 ee is used, the reaction still affords the final spiro compound in almost diastereo- and enantiopure form.

Original languageBritish English
Pages (from-to)1318-1325
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
StatePublished - Mar 2011

Keywords

  • Diastereoselectivity
  • Enantioselectivity
  • Michael addition
  • Organocatalysis
  • Spiro compounds

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