Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

Jingya Yang, Shaoxiang Wu, Fu Xue Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3′-di(1-adamantyl)-1,1′- binaphthyl-2,2′-diylphosphoric acid and NaOH, β-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 °C in toluene.

Original languageEnglish
Pages (from-to)2725-2728
Number of pages4
JournalSynlett
Issue number18
DOIs
Publication statusPublished - 2010

Keywords

  • 1,4-addition
  • asymmetric catalysis
  • enones
  • nitriles
  • phosphates

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