4.4 Article

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

Journal

SYNLETT
Volume 29, Issue 16, Pages 2171-2175

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610551

Keywords

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

Funding

  1. National Research, Development and Innovation Office of Hungary (NKFIH) [PD129652, K104528]
  2. Richter Gedeon Talentum Foundation

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Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantioselective 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.

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