53344-40-4

Upstream product

• 110-91-8 morpholine 
• 611-70-1 phenyl isopropyl ketone 

Downstream Products

• 53344-42-6 8,8-dimethyl-9-morpholin-4-yl-4,6,9-triphenyl-1-oxa-spiro[4.4]nona-3,6-dien-2-one 
• 53344-41-5 5-[(2,2-dimethyl-3-morpholin-4-yl-3-phenyl-cyclopropyl)-phenyl-methylene]-4-phenyl-5H-furan-2-one 
• 96921-34-5 4-(2-methyl-1-phenyl-propyl)-morpholine 

Relevant academic research and scientific papers

New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes

The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided γ-keto esters in good yields. A full investigation of the effects of solvents, catalysts, enamines and aryldiazoacetates on the reaction was carried out. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a γ-keto ester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed. Chiral dirhodium and copper catalysts were examined and found to provide γ-keto esters with no enantioselectivity. The result could be rationalized based on the proposed reaction mechanism. Attempts to trap the enamine intermediate with several electrophilic reagents were not successful.

Improved Titanium Tetrachloride Procedure for Enamine Synthesis.II.Scope of the Reaction

The scope of enamine formation by a procedure where the carbonyl compound is added to a preformed titanium tetrachloride-amine complex was investigated with a series of different types of carbonyl compounds and two secondary amines (morpholine and pyrrolidine).The carbonyl compounds include aldehydes, cyclic ketones and some substituted aryl alkyl ketones.Yields of isolated products were in the range 67-100 percent with the exception of the pyrrolidine enamine from camphor which gave 53 percent of the isolated product.