A New Organocatalyst for the Strecker Reaction

Significance

A new organocatalyst has been developed which contains a glycosyl amine and a planar-chiral [2.2]paracyclophane but no hydrogen-bond-donor or Brønsted acidic functionalities. The catalyst was used in an enantioselective Strecker reaction where HCN was generated in situ from Me₃SiCN and methanol. Imines derived from aliphatic aldehydes afford products in good yields with high enantioselectivities. The reaction with aromatic aldimines, on the contrary to other reported enantioselectively catalyzed Strecker reactions, gave slightly lower enantioselectivity.