225796-45-2

Upstream product

• 13996-78-6 N-isopropyl-D-glucosamine 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 225796-44-1 Acetic acid (2R,4aR,7R,8R,8aS)-6-acetoxy-7-isobutyrylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 

Downstream Products

• 225796-46-3 2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline 

Relevant academic research and scientific papers

Palladium-catalysed asymmetric allylic alkylation using new chiral phosphinite-nitrogen ligands derived from D-glucosamine

Novel phosphinite-nitrogen chiral ligands synthesized from D-glucosamine furnish a high level of enantiomeric excess (up to 96% ee] in palladium-catalysed allylic alkylation.

Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinite-oxazoline ligands derived from D-glucosamine

Novel 2-alkyl- or 2-aryl-4,5-(4,6-O-benzylidene-3-O-(diphenylphosphino)- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazolines (5a-f) have been prepared from D-glucosamine hydrochloride. They work effectively as chiral ligands and provide a high level of enantiomeric excess in palladium-catalyzed allylic alkylation and amination reactions. The allylic alkylation of 1,3-diphenyl-3- acetoxyprop-1-ene with dimethyl malonate proceeds smoothly in the presence of 0.25 mol % [Pd(η3C3H5)Cl]2 and the chiral ligand 5a having the smallest substituent on oxazoline at 0 °C within 6 h to furnish the highest enantiomeric excess (96% ee). The ligand 5a is also effective for the Pd- catalyzed amination of ethyl 1,3-diphenylprop-2-enyl carbonate, leading to the corresponding allylic amine in 94% ee. The full scope and limitations using ligands 5a-f in the allylic substitution reactions are described.