Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis–Hillman reaction

Chiral quinuclidine derivatives were employed as catalysts in the one-pot, three-component aza-Baylis–Hillman reaction between arylaldehydes, tosylamide and alkyl acrylates or acrylonitrile. A sterically non-hindered tricyclic derivative of quinidine was found to be the most efficient catalyst in transferring its chiral information. High conversions were ensured by using a catalytic amount of titanium isopropoxide and by the addition of molecular sieves (4 Å). The adducts formed, α-methylene-β-amino acid derivatives, were obtained in good yields (up to 95%) and in enantioselectivities up to 74%.