AgOAc-catalyzed asymmetric amination of glycine Schiff bases with azodicarboxylates

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6866-6868

  Chen, Qing An ^a   Zeng, Wei ^a   Zhou, Yong Gui ^a,b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric amination; Azodicarboxylates; Glycine Schiff bases; Silver acetate

Indexed keywords

ACETATE SILVER; AZO COMPOUND; AZODICARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; SCHIFF BASE; SILVER DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 70350028724     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.124     Document Type: Article

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44. General procedure for the AgOAc-catalyzed asymmetric amination reactions (Table 2, entry 1): Ligand (0.0075 mmol) and AgOAc (1.2 mg, 0.007 mmol) were placed in a dried Schlenk tube under a nitrogen atmosphere and toluene (2.0 mL) was added. The mixture was stirred at room temperature for about 0.5 h. After it was cooled to the indicated temperature, benzophenone imine glycine methyl ester (0.23 mmol) was added followed by diethyl azodicarboxylate (0.276 mmol). Progress of the Ag-catalyzed amination reaction was typically monitored by TLC analysis. Upon consumption of the limiting reagent, the pure adducts were purified by column chromatography on silica gel.
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