Straightforward access to enantioenriched pyrazyl alcohols using chiral organomagnesiates

Olivier Payen , Floris Chevallier (1) , Florence Mongin (1) , Philippe C. Gros

1 ISCR - Institut des Sciences Chimiques de Rennes

The clean iodine-metal exchange of iodopyrazine and subsequent enantioselective addition of the intermediate pyrazyl magnesiate to aldehydes using ((R,R)-TADDOLate)Bu2MgLi2 is reported. New chiral pyrazylalcohols were obtained in enantiomeric excesses of up to 90%.

Mots clés: ENANTIOSELECTIVE ADDITION; ABSOLUTE-CONFIGURATION; PYRIDYL ALCOHOLS; HYDROGENATION; KETONES; DIETHYLZINC; ALDEHYDES; FUNCTIONALIZATION; METALATION; CATALYSTS

Domaines: Chimie organique

Olivier Payen, Floris Chevallier, Florence Mongin, Philippe C. Gros. Straightforward access to enantioenriched pyrazyl alcohols using chiral organomagnesiates. Tetrahedron: Asymmetry, 2012, 23 (34), pp.1678-1682. ⟨10.1016/j.tetasy.2012.11.003⟩. ⟨hal-00813094⟩