Development of Mefloquine-Based Bifunctional Secondary Amine Organocatalysts for Enantioselective Michael and Friedel–Crafts Reactions

The
chiral framework based on 11-aminomefloquine has been utilized
for the first time to construct bifunctional organocatalysts. These
catalysts demonstrate high enantioselectivity in both Michael additions
and Friedel–Crafts reactions across a variety of substrates,
achieving up to >99% ee. The distinctive feature is the incorporation
of a secondary amine group, offering unique tight hydrogen-bonding
capabilities in the protonated state, as supported by DFT computation.
The diversity of these organocatalysts suggests their broad applicability
across multiple reaction classes.