118673-07-7

Upstream product

• 106-95-6 allyl bromide 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 137960-20-4 (E)-(2R,3R)-3-Allylamino-2-methyl-5-phenyl-pent-4-enethioic acid S-tert-butyl ester 
• 83575-93-3 (1E,3E,5E/Z)-4-Aza-1-phenyl-1,3,5-heptatriene 
• 137960-29-3 (3R,4R)-3-Methyl-4-phenethyl-1-propyl-azetidin-2-one 
• 137960-26-0 (3R,4R)-1-Allyl-3-methyl-4-((E)-styryl)-azetidin-2-one 
• 118673-22-6 (3R,4S)-3-Phenoxy-1-((E)-propenyl)-4-((E)-styryl)-azetidin-2-one 
• 889686-17-3 dimethyl (2E)-1-(allyl(benzyl)amino)-3-phenylprop-2-enylphosphonate 
• 877825-98-4 dimethyl (2E)-1-[allyl(chloroacetyl)amino]-3-phenyl-2-propenylphosphonate 
• 887500-72-3 dimethyl (2E)-1-(allylamino)-3-phenylprop-2-enylphosphonate 
• 86386-72-3 N-(3-phenylallyl)-allylamine 

Relevant academic research and scientific papers

Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides

Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.

An effective method to prepare imines from aldehyde, bromide/epoxide, and aqueous ammonia

A three-component reaction of aldehydes, alkyl bromides, and ammonia to form imines was studied. Aqueous ammonia was applied as the nitrogen source and solvent in the reaction. For the aromatic aldehyde, the product yields are good to excellent and the reaction conditions are mild to be compatible with a range of functional groups. The reaction of aldehydes and aqueous ammonia with epoxides was also studied and imines bearing a vicinal hydroxyl group can be obtained efficiently and regioselectively. And studies showed that this method allows the synthesis of primary amines and especially 1,2-amino alcohol selectively in high yield. It is proposed that the reaction pathway might involve a key intermediate of hydrobenzamide.

One-pot synthesis of N-chloroacetyl 1-aminoalkyl phosphonates - Precursors of 4-phosphono-β-lactams

4-Phosphono-β-lactams are synthesized via a three-step sequence, including final formation of the C3-C4 bond through a phosphorus-stabilized carbanion. The chlorinated precursors can be synthesized via two different methods: a one-pot N-acylation of an aromatic imine followed by addition of a trialkyl phosphite or phosphonylation of a suitable imine followed by N-acylation in a separate reaction step. The former method was preferred because of the ease of the reaction and the good yields obtained. Georg Thieme Verlag Stuttgart.

Diazoketones as precursors in β-lactam synthesis. New insights into the mechanism of the photochemically induced Staudinger reaction

Diazoketones 1-3, derived from suitably protected amino acids (Ala, Val and Tle), have been photochemically rearranged in the presence of imines leading exclusively to trans-arranged 4-aryl- and cinnamoyl-substituted β-lactams 17-33 with up to 84% yield. Selectivities were dependent on the steric demand of the amino acid side-chain ranging from 65:35 to 90:10. The relative configurations were proved by several X-ray crystal structures and comparison of NMR spectra. Further reactions of the azetidinones at position C-4 have been performed: electron-rich aryl substituents (e.g., 4-methoxyphenyl, furyl and thienyl) could be degraded to carboxylic acids 34 and 35 which were further transformed to acetoxy derivatives (compounds 36 and 37) in a Kolbe reaction of type II. The cinnamoyl group could be oxidized to the formyl group by ozonolysis (→38,39). The mechanism of the photochemically induced β-lactam formation is discussed in detail.

Stereocontrolled Synthesis of N-Vinyl-, N-(1'-Propenyl)-, and N-Unsubstituted-β-lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction

2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale.Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-β-lact

Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines

The reaction of S-tert-butyl thiopropionate with a number of N-benzyl or N-allyl aldimines (4) as promoted by the chiral diazaborolidine 1 and triethylamine afforded the β-amino acid esters 5 with high diastereoselectivity and enantioselectivity, providin

2-AZA-1,3-DIENES AS NOVEL PRECURSORS FOR THE SYNTHESIS OF N-UNSUBSTITUTED β-LACTAMS. A THREE STEP SYNTHESIS OF 4-ACETOXY-3-PHENOXY-2-AZETIDINONE

2-Aza-1,3-dienes, prepared in excellent yields from aldehydes and readily available allylamine, were utilized to synthesize N-(1-propenyl)-β-lactams.Oxidative cleavage of the N-protecting group produced N-unsubstituted β-lactams. 4-Acetoxy-3-phenoxy-2-aze