Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents

Jezabel Praz, Laure Guénée, Sarwar Aziz, Albrecht Berkessel, Alexandre Alexakis

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Novel endo,endo-2,5-diaminonorbonane-derived tertiary C 2- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.

Original languageEnglish
Pages (from-to)1780-1790
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number9
DOIs
StatePublished - 18 Jun 2012
Externally publishedYes

Keywords

  • asymmetric catalysis
  • bromine-lithium exchange
  • deprotonation
  • endo,endo-2,5-diaminonorbonane derivatives
  • nucleophilic addition
  • organolithium compounds

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