@misc{10481/106445,
year = {2025},
month = {7},
url = {https://hdl.handle.net/10481/106445},
abstract = {Background: Carbohydrate-derived chiral ligands are promising tools in asymmetric catalysis due to their structural diversity, chirality, and availability. However, ligands based
on galactose or sorbose have been scarcely explored in the enantioselective addition of
dialkylzinc reagents to aldehydes. Methods: A series of chiral diols and β-amino alcohols was synthesized from methyl D-glucopyranoside, methyl D-galactopyranoside, and
D-fructose. These ligands were tested in the titanium tetraisopropoxide-promoted enantioselective addition of diethylzinc to aromatic and aliphatic aldehydes. Results: Several
ligands, particularly those with a D-fructopyranose backbone, exhibited excellent catalytic
activity, with conversion rates up to 100% and enantioselectivities up to 96% ee. Notably,
this study reports for the first time the use of β-amino alcohols derived from fructose and
sorbose in this transformation. Conclusions: Carbohydrate-based ligands represent effective, inexpensive, and structurally versatile scaffolds for developing highly enantioselective
catalysts, expanding the utility of sugars in asymmetric organometallic reactions.},
organization = {Junta de Andalucía (P09-FQM-4498)},
publisher = {MDPI},
keywords = {Carbohydrates},
keywords = {Asymmetric catalysis},
keywords = {Titanium},
title = {Carbohydrate-Based Chiral Ligands for the Enantioselective Addition of Diethylzinc to Aldehydes},
doi = {10.3390/ph18081088},
author = {López-Delgado, Francisco Javier and Lo Re, Daniele and Franco Montalbán, Francisco and Tamayo Torres, Juan Antonio},
}