Asymmetric Synthesis of Structurally Sophisticated Spirocyclic Pyrano[2,3-<i>c</i>]pyrazole Derivatives Bearing a Chiral Quaternary Carbon Center

Abstract

A carbene-catalyzed enantio- and diastereoselective [2 + 4] cycloaddition reaction is developed for quick and efficient access to structurally complex multicyclic pyrano[2,3-c]pyrazole molecules. The reaction tolerates a broad scope of substrates bearing various substitution patterns, with the multicyclic pyrano[2,3-c]pyrazole products afforded in generally good to excellent yields and optical purities. The chiral molecules obtained from this approach has found promising applications in the development of novel bacteriacides for plant protection.