Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes: Development, mechanism and DFT calculations

Ismail Ibrahem, Peter Hammar, Jan Vesely, Ramon Rios, Lars Eriksson, Armando Córdova

Research output: Contribution to journalArticlepeer-review

86 Scopus citations

Abstract

The development and mechanism of the highly chemo- and enantioselective organocatalytic hydrophosphination reaction of α,β-unsaturated aldehydes is presented. The reactions are catalyzed by protected chiral diarylprolinol derivatives and give access to optically active phosphine derivatives in high yields with upto 99% ee. The organocatalytic addition of other phosphorus nucleophiles was also investigated. The origin of the high enantioselectivity for the reaction with diphenylphosphine as the nucleophile is investigated by density functional theory calculations.

Original languageBritish English
Pages (from-to)1875-1884
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number11-12
DOIs
StatePublished - 4 Aug 2008

Keywords

  • Asymmetric catalysis
  • Chiral phosphines
  • DFT calcuations
  • Hydrophoshination
  • Organocatalysis
  • α,β-unsaturated aldehydes

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