Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

Zhong Xiu Chen, Teng Ai, Parminder Kaur, Guigen Li

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral β-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.

Original languageEnglish (US)
Pages (from-to)1079-1081
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number9
DOIs
StatePublished - Mar 4 2009

Keywords

  • Dimethyl malonate
  • N-Phosphonyl imines
  • Phosphoramide
  • β-Aminomalonates

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