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• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 109388-02-5 1-(4-methoxyphenyl)-4-phenyl-3-vinylazetidin-2-one 
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• 105-54-4 butanoic acid ethyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis, reactions and antimicrobial activity of 3-vinyl-2-azetidinones

Stereocontrolled synthesis of 3-vinyl-2-azetidinones has been achieved by the condensation of imines and conjugated acids using phosphorus oxychloride. Transformation of these compounds to other useful intermediates has also been accomplished. Some of the

Soluble-polymer-supported synthesis of β-lactams on a modified poly(ethylene glycol)

A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of β-lactams. The monomethylether of PEG (MeOPEG) with an average Mw of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several β-lactams by enolate/imine condensation and ketene/ imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the β-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.

β-Tosylethylamine: A Useful Reagent for Preparation of N-Protected Amides, Carbamates, and Related Compounds. Application to Synthesis of β-Lactams

Readily prepared β-tosylethylamine (3) can be used to synthesize N-tosylethyl (TSE)-protected amido compounds and β-lactams, which can be deprotected under mild conditions with potassium tert-butoxide.

Reaction of Silyl Ketene Acetals with N-Trimethylsilyl Imines: a Route to N-Unsubstituted Azetidin-2-ones

Reaction of N-trimethylsilyl imines with silyl ketene acetals in the presence of ZnI2 and t-butyl alcohol, followed by treatment in situ of the intermediate N-silyl β-aminoesters with MeMgBr, leads to N-unsubstituted azetidin-2-ones in good yield.

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.