17324-19-5

Upstream product

• 538-51-2 benzylidene phenylamine 
• 105-54-4 butanoic acid ethyl ester 
• 156662-11-2 (E)-2-(1-(tert-butyldimethylsilyloxy)but-1-enylthio)pyridine 
• 37612-62-7 1-butyryl-3,5-dimethyl-1H-pyrazole 
• 33812-87-2 trans-1,4-diphenyl-3-vinylazetidin-2-one 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 26074-52-2 2-bromo-butyryl bromide 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 37746-78-4 4-bromo-trans-crotonic acid ethyl ester 

Relevant academic research and scientific papers

Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates

Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.

DiastereoselectivesSynthesis of trans β-lactams on soluble polymer support

Liquid-phase synthesis of trans β-lactams was accomplished through both PEG-supported imine and PEG-bound auxiliary methodologies. The trans diastereoselectivity is explained by a chair-like transition state involving the imine and the Z-enolate. Georg Thieme Verlag Stuttgart.

An efficient and diastereoselective synthesis of trans β-lactams and β-aminocarbonyl compounds

Efficient and diastereoselective syntheses of trans β-lactams and anti β-aminocarbonyl compounds from carboximide 1 and imines 2 under the classical Reformatsky reaction conditions are described. An enolate-imine mechanism has been proposed for this react

Highly trans-selective synthesis of β-lactams by tandem phenoxide anion-catalyzed Mannich-type addition and cyclization

Highly trans-selective synthesis of β-lactams by tandem Lewis base-catalyzed Mannich-type addition and cyclization was established; that is, reaction of benzylideneanilines and trimethylsilyl enolates derived from S-ethyl thioates proceeded smoothly to af

Microwave-assisted rapid and simplified hydrogenation

Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

Synthesis of Optically Active β-Lactams by the Reaction of 2-Acyl-3-phenyl-l-menthopyrazoles with C=N Compounds

The reaction of 1-acyl-3,5-dimethyIpyrazoles 1 with C=N compounds was kinetically controlled with syn stereoselectivity through a lithium enolate intermediate using lithium diisopropylamide. In contrast, the anti stereoselective reaction of 1 was caused b

REACTIVITY OF THE PYRIDYLTHIOSILYL ENOL ETHER - ROUTE TO Β-LACTONE AND Β-LACTAM

A simple and facile method for β-lactone and β-lactam syntheses based on a Lewis acid promoted pyridylthiosilyl enol ether (1) addition to an aldehyde or Schiff base is described.

N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams

Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams.The stereochemical course of the reaction depends on the ester enolate geometry.Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams.The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis.The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-imine condensations are also discussed.