Chiral N-phosphonyl imine chemistry: Asymmetric additions of ester enolates for the synthesis of β-amino acids

Jianlin Han, Teng Ai, Thao Nguyen, Guigen Li

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

Chiral phosphonyl imines attached by 1-naphthyl protection group were found to react with lithium ester enolates smoothly and give chiral β-amino esters in good yields (70-88%) and up to excellent diastereoselectivity (>99:1 dr). Triisopropoxytitanium (IV) chloride was found to enhance diastereoseletivity when used as the Lewis acid promoter. The chiral auxiliary can be readily removed by treating with HBr to give free amino esters. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample. This reaction provides an easy access to β-amino acid derivatives.

Original languageEnglish
Pages (from-to)120-126
Number of pages7
JournalChemical Biology and Drug Design
Volume72
Issue number2
DOIs
StatePublished - Aug 2008

Keywords

  • Chiral N-phosphonyl imines
  • Chiral phosphoramide
  • Lithium enolate
  • Triisopropoxytitanium(IV) chloride
  • β-amino acid

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