Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process.
Lewis acid catalyzed reaction of 2-furaldehyde and secondary amines results in the formation of 4,5-diaminocyclopent-2-enones exclusively as the trans diastereomers: computational studies support the stereochemistry of the adducts as arising from a thermal conrotatory pi4a electrocyclization of an initial ring-opened intermediate (a deprotonated Stenhouse salt).
Li
Sze-Wan
SW
Department of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, Canada.
Batey
Robert A
RA