Enantioselective Construction of Indolizines Containing Vicinal Diaxial Chirality

Abstract

Aromatic compounds featuring vicinal diaxial chirality are prevalent structural motifs in synthetically important substances. However, the synthesis of these compounds is limited by challenges in achieving stereoselectivity at dynamic vicinal diaxially chiral centers, with current studies primarily focusing on the formation of homoannular vicinal diaxially chiral molecules. In this work, we present a copper-catalyzed cycloisomerization method that successfully constructed indolizines with vicinal diaxial chirality existing across the ring under mild reaction conditions, yielding the desired products in high yields and enantioselectivity. Notably, this innovative approach serves as a versatile strategy for generating various vicinal diaxially chiral structures, providing extra avenues for the synthesis of stereochemically complex molecular frameworks. Furthermore, this unique scaffold demonstrated a remarkable circularly polarized luminescence property, with a g_lum value reaching up to 0.01, indicating significant potential for applications in chiral organic optoelectronic materials.