Enantioselective Construction of Indolizines Containing Vicinal Diaxial Chirality

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 glum value reaching up to 0.01, indicating significant
potential for applications in chiral organic optoelectronic materials.