Chiral N-phosphonyl imine chemistry: Asymmetric addition of ketone-derived enolates for the synthesis of β-amino ketones

Jianlin Han, Teng Ai, Guigen Li

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

New chiral N-phosphonyl imines have been synthesized in good yields under convenient reaction conditions. These chiral N-phosphonyl imines can serve as efficient electrophiles for asymmetric addition reactions with lithium ketone enolates. Good chemical yields and excellent diastereoselectivities were obtained for twelve examples. The N-1-naphthyl group of the chiral auxiliary was found to be superior to its benzyl counterpart in controlling the diastereoselectivity for this reaction. The chiral auxiliary can be readily removed by treatment with aqueous HBr in methanol at room temperature to give free β-amino ketones in high yields.

Original languageEnglish
Article numberM01208SS
Pages (from-to)2519-2526
Number of pages8
JournalSynthesis
Issue number16
DOIs
StatePublished - Aug 18 2008

Keywords

  • C- symmetric diamine
  • N-phosphonyl imine
  • Phosphoramide
  • β-amino ketone

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