Asymmetric hydrophosphylation of chiral n-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates

Parminder Kaur, Walter Wever, Trideep Rajale, Guigen Li

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α-amino phosphonate into its authentic N-Cbz derivative.

Original languageEnglish
Pages (from-to)314-319
Number of pages6
JournalChemical Biology and Drug Design
Volume76
Issue number4
DOIs
StatePublished - Oct 2010

Keywords

  • N-phosphonyl imine
  • chiral α-amino phosphonates

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