Design and Synthesis of Phenylcyclopropane-based Chiral Amine Catalysts and Their Application in Asymmetric Reactions

Chiral amine catalysts are widely utilized in various asymmetric reactions. Among them, binaphthyl-based secondary amine catalysts show unique reactivity and unusual stereoselectivity in comparison with frequently used L-proline and its derivatives. In spite of their utility, however, asymmetric reactions employing binaphthyl-based amines are rare because of their synthetic inefficiency. In this context, we have developed chiral secondary amine catalysts based on a phenylcyclopropane scaffold as a novel chiral motif. Newly synthesized amine catalysts function as effective catalysts for several asymmetric reactions. In addition, the phenylcyclopropane-based amino sulfonamide was found to be an effective catalyst for the syn-selective Mannich reaction and conjugate addition with alkynyl Z-ketimines.

Automated summary

Binaphthyl-based amine catalysts exhibit unique reactivity and stereoselectivity in asymmetric reactions, but are rarely used due to their synthetic inefficiency. Chiral secondary amine catalysts based on a phenylcyclopropane scaffold have been developed and show high catalytic activity in several asymmetric reactions.