Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines

Ophélie Quinonero (1) , Marion Jean (1) , Nicolas Vanthuyne (1) , Christian Roussel (1) , Damien Bonne (1) , Thierry Constantieux (1) , Cyril Bressy (1) , Xavier Bugaut (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

Suitably substituted enantioenriched 4-aryl-1,4-dihydro-pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4-arylpyridines with central-to-axial chirality conversion. Moderate to complete conversion percentages (cp) were observed, and a model for the conversion of chirality is discussed.

Mots clés: atropisomers; chirality conversion; enantioselectivity; organocatalysis; pyridines

Domaines: Chimie organique

Ophélie Quinonero, Marion Jean, Nicolas Vanthuyne, Christian Roussel, Damien Bonne, et al.. Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines. Angewandte Chemie International Edition, 2016, 55, ⟨10.1002/anie.201509967⟩. ⟨hal-01323419⟩