N-Phosphinyl Imine Chemistry (I): Design and Synthesis of Novel N-Phosphinyl Imines and their Application to Asymmetric aza-Henry Reaction

Suresh Pindi, Parminder Kaur, Gaurav Shakya, Guigen Li

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

Novel chiral N-phosphinamide and N-phosphinyl imines have been designed, synthesized and applied to asymmetric aza-Henry reaction to give excellent chemical yields (92%- quant.) and diastereoselectivity (91% to >99%de). The reaction showed a great substrate scope in which aromatic/aliphatic aldehyde- and ketone-derived N-phosphinyl imines can be employed as electrophiles. The chiral N-phosphinamide can be stored at room temperature for more than 2 months without inert gas protection, and chiral N-phosphinyl imines were also proven to be highly stable at room temperature for a long period under inert gas protection. The N-phosphinyl group enabled the product purification to be performed simply by washing crude product with EtOAc and hexane. This reaction joined other eight GAP (Group-Assistant-Purification) chemistry processes that were developed in our laboratories. The absolute configuration has been unambiguously determined by converting a β-nitroamine product into a known N-Boc sample.

Original languageEnglish
Pages (from-to)20-29
Number of pages10
JournalChemical Biology and Drug Design
Volume77
Issue number1
DOIs
StatePublished - Jan 2011

Keywords

  • Aza-Henry reaction
  • Chiral N-phosphinamide
  • GAP (Group-Assistant-Purification) chemistry
  • N-phosphinyl imines

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