Synthesis of hemilabile P,N-ligands with a pentane-2,4-diyl backbone

Gergely Farkas, Zsófia Császár, Szabolcs Balogh, Imre Tóth, József Bakos

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9 Citations (Scopus)

Abstract

A general and convenient two-step synthetic method has been developed for the preparation of a novel class of aminoalkyl-phosphine type compounds, which involves nucleophilic ring-opening of cyclic sulfate esters. The ring-opening step was performed using several different aliphatic and aromatic amines to produce aminoalkyl sulfates that were reacted with LiPPh2 to give the corresponding P,N-ligands. The desymmetrization procedure affords an easy route to synthesize enantiomerically pure pentane-2,4-diyl based P,N-ligands with a highly tunable structure. The ligands derived from primary amines have a stereogenic N-atom that can be useful in asymmetric catalytic syntheses.

Original languageEnglish
Pages (from-to)4120-4122
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number30
DOIs
Publication statusPublished - Jul 23 2014

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Keywords

  • Asymmetric synthesis
  • Azetidine
  • Cyclic sulfates
  • P,N-ligands
  • Stereogenic N-atom

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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