Abstract
We had synthesized a series of β-hydroxy sulfonamides D-glucosamine and applied them as ligands in the titanium tetraisopropoxide-promoted enantioselective addition of phenylacetylene and hexyne-1 to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-3,5-bis(ditrifluoromethyl)benzenesulfonamido-D-glucosamine derivative performed best and we choose it as the most efficient ligand for the addition of phenylacetylene and hexyne-1 to aldehydes. High enantiomeric excesses, up to 96%, were obtained for some aromatic aldehydes.
Keywords: Aldehydes, D-glucosamine, dialkylzinc, enantioselective, hexyne-1, phenylacetylene.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
16