Abstract
Highly enantioselective asymmetric Baylis-Hillman reactions employing (3R, 8R, 9S) -10, 11-dihydro-3, 9-epoxy-6'-hydroxy-cinchonane, β-isocupreidine (β-ICD), as a chiral amine catalyst and 1, 1, 1, 3, 3, 3-hexafluoroisopropyl acrylate (HFIPA) as an activated alkene are described for aldehydes including chiral N-Boc-α-amino aldehydes and aromatic N-diphenylphosphinoyl imines. The key features of this β-ICD-HFIPA method and a plausible reaction mechanism governed by hydrogen bonding are presented.
