Unveiling the Correlation between the Alkyl Chain Length of Amphiphiles in Chiral Supramolecular Nanocatalysts and Enantioselectivity.

The correlation between the molecular structure of chiral amphiphiles and the enantioselectivity exhibited by their corresponding chiral supramolecular assemblies is a critical factor in enabling asymmetric catalysis. Herein, the self-assembly of l/d-phenylglycine-based amphiphiles (l/d-PhgC, = 8, 12, 15, 16, 17, 18, and 20) with varying alkyl chain lengths into chiral supramolecular catalysts via Cu(II) coordination is reported, and their enantioselectivity in catalyzing the asymmetric Diels-Alder reaction is systematically investigated. Among the series, the l-PhgC-based supramolecular catalyst achieves exceptional enantioselectivity (96% ), whereas analogs with shorter ( < 16) or longer ( > 18) alkyl chains display diminished selectivity or even racemic outcomes.

Metal Ion-Mediated Supramolecular Nanotube Catalyst for Enantioselective Reactions.

Rational control over the morphologies of supramolecular assemblies for asymmetric catalysis with enhanced enantioselectivity represents a pivotal challenge in the realm of synthetic chemistry and material technology. Herein, Cu(II) ion-mediated supramolecular nanostructures assembled from chiral amino acid-based amphiphiles (l/d-AlaC) are fabricated as chiral catalysts for Diels-Alder cycloaddition between aza-chalcone and cyclopentadiene. In particular, compared with the supramolecular nanosheet formed by l/d-AlaC without Cu(II) ions, we found that the l/d-alanine chiral amphiphile can form supramolecular nanotubes with a multilayer structure and with the thickness of the tubular wall about 15 nm through the transition from a nanoribbon to tubular structure in the presence of Cu(II) ions.