39629-30-6

Upstream product

• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 67-56-1 methanol 
• 538-51-2 benzylidene phenylamine 
• 53429-22-4 methyl 2-bromozincacetate 
• 3768-55-6 N-trimethylsilylaniline 
• 96-32-2 bromoacetic acid methyl ester 
• 7440-66-6 zinc 
• 79-20-9 acetic acid methyl ester 
• 35401-49-1 -methyl 3-phenyl-3-(phenylamino) acrylate 
• 22086-33-5 1,4-diphenyl-3-dichloro-azetidine-2-one 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 867-89-0 1-dimethylamino-1-methoxyethylene 

Downstream Products

• 855398-32-2 3-(N-methoxyoxalyl-anilino)-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

One-Pot Silyl Ketene Acetal-Formation Mukaiyama-Mannich Additions to Imines Mediated by Trimethylsilyl Trifluoromethanesulfonate

In the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base, thioesters are readily converted into silyl ketene acetals in situ and undergo Mukaiyama-Mannich addition to N-phenylimines in one pot. The silyl triflate appears to play

Synthesis of a series of novel chiral Lewis base catalysts and their application in promoting asymmetric hydrosilylation of β-enamino esters

A series of novel chiral Lewis base catalysts were synthesized from l-serine and applied in the hydrosilylation of β-enamino esters, in which the optimal one promoted the reactions to afford a wide variety of β-amino esters in good yields with good enantioselectivities. It is noteworthy that several cyclic substrates were hydrosilylated under the optimal conditions to give the cyclic β-amino esters with high yields, good diastereoselectivities as well as good ee values. The Royal Society of Chemistry 2013.

PREPARATION OF ORGANOZINC HALIDES FROM REACTIVE HALOGEN COMPOUNDS AND THEIR USE

A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.

Multiple component reactions: An efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of β-amino carbonyl libraries

Multiple-component condensations (MCC) where three or more reactants combine to afford a new core structure possessing the molecular features of its composite building blocks is a powerful method for the preparation of molecular diversity. We have developed an efficient, nickel-catalyzed, Reformatsky-type three-component condensation (3CC) reaction that affords β-amino carbonyl compounds. The scope of the reaction is demonstrated both in the gram and microscale settings; 15 β-amino esters, amides, and a ketone were prepared efficiently at the mmol scale, and a library of 64 β-amino carbonyl compounds was generated at the μmol scale.

A simple one-pot three-component reaction for preparation of secondary amines and amino esters mediated by lithium perchlorate

The one-pot synthesis of several secondary amines and secondary amino esters are reported. Treatment of aldehydes (aliphatic or aromatic) with (trimethylsilyl)alkylamines, in the presence of 5 M lithium perchlorate in diethyl ether gives intermediate imines. Reaction of these intermediate imines with different nucleophiles and functionalized organozinc reagents, BrZnCH2COOR, produce a variety of secondary amines and N-alkyl- or N-arylamino esters in good yields.

Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of 2 and TMS-CN under Almost Neutral Conditions

In the presence of catalytic amount of a transition metal compound such as 2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields.In the coexistence of catalytic amounts of Rh

A Convenient Synthesis of β-Aminoesters. The Reaction of Imines with Ketene Silyl Acetals Catalyzed by Phosphonium Salts

In the presence of a catalytic amount of a diphosphonium salt, the reaction of various imines, including 2--pyridine, with ketene silyl acetals proceeded smoothly to afford the corresponding β-aminoesters in good yields.

High-Pressure-Promoted (2 + 2) Cycloadditions of Imines with Electron-Rich Alkenes. A Simple Route to Azetidines and β-Amino Carbonyl Compounds

The synthetic scope of high-pressure-promoted (2 + 2) cycloadditions between imines and electron-rich alkenes has been investigated.For the first time it has been possible to isolate an azetidine from the reaction of the strong electron-rich 1-pyrrolidino

Hydrolytic behavior of two β-lactams and their corresponding imidate salts. New evidence for stereoelectronic control

The basic hydrolysis and the concurrent carbonyl-oxygen exchange of 18O-labelled N-phenyl-4-phenyl-2-azetidinone (5*) and N-2,6-dimethylphenyl-2-azetidinone (6*) have been studied. β-Lactam 5* was easily hydrolysed and showed no carbonyl-oxygen exchange with 0.1 N sodium hydroxide (dioxane - water, 9:1).Under the same conditions, β-lactam 6* gave no exchange and was found resistant to basic hydrolysis.Hydrolysis and exchange was observed when 6* was refluxed with 0.1 N and 1 N sodium hydroxide in water.The hydrolysis of the corresponding imidate salts 7 and 8 was also investigated.Under basic conditions, salt 7 gave and 8:2 mixture of ester amine 9 and β-lactam 5, while under acidic conditions the hydrochloride salt of ester amine 9 was the only product.Under basic conditions, the imidate salt 8 produced only the β-lactam 6, and under acidic conditions, a 3:7 mixture of the hydrochloride salt of 10 and β-lactam 6.Under stronger acidic conditions (>/=3 N HCl), 8 gave only the starting β-lactam 6.The results of these hydrolysis reactions are easily explained on the basis of the stereoelectronic theory for the cleavage of tetrahedral intermediates, and by taking into account that the nitrogen of tetrahedral intermediates must be either protonated under acidic conditions, or hydrogen bonded with the solvent under basic conditions in order to observe the cleavage of the C-N bond.