Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates

Teng Ai, Guigen Li

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give α,β-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample.

Original languageEnglish
Pages (from-to)3967-3969
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number14
DOIs
StatePublished - Jul 15 2009

Keywords

  • Glycine enolate
  • N-Phosphonyl imines
  • Phosphoramide
  • α,β-Diamino ester

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