Copper-catalyzed remote asymmetric yne-allylic substitution: construction of thiazolone derivatives with adjacent chiral centers

Abstract

The synthesis of chiral thiazolones is of paramount importance due to their extensive biological activities and potential applications in the pharmaceutical field. This study introduces a copper-catalyzed remote asymmetric yne-allylic substitution method for the construction of thiazolone derivatives with adjacent chiral centers. The selectivity of this transformation is highly challenging due to the complexity of controlling multiple stereocenters in a single reaction step. In light of the above, a highly diastereo- and enantioselective copper-catalyzed remote asymmetric yne-allylic substitution of yne-allylic esters and thiazolones was developed. Our method demonstrates good regioselectivity and enantioselectivity, providing a direct route to complex molecular architectures with potential pharmaceutical relevance. The success of this strategy underscores the significance of remote functionalization in accessing biologically relevant molecules and highlights the potential of copper catalysis in asymmetric synthesis.