Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions

Béla Mátravölgyi, Szilvia Deák, Zsuzsanna Erdélyi, Tamás Hergert, Péter Ábrányi-Balogh, F. Faigl

Research output: Contribution to journalArticle

Abstract

Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantio-selective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric-atropisomeric ligands.

Original languageEnglish
Article numberst-2018-d0265-c
Pages (from-to)2171-2175
Number of pages5
JournalSynlett
Volume29
Issue number16
DOIs
Publication statusPublished - Jan 1 2018

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Keywords

  • amino alcohols
  • asymmetric catalysis
  • atropisomerism
  • enantioselectivity
  • ligands
  • phenylpyrrole

ASJC Scopus subject areas

  • Organic Chemistry

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