92287-44-0

Upstream product

• 873-67-6 benzonitrile oxide 
• 106-99-0 buta-1,3-diene 
• 821-06-7 (E)-1,4-dibromobutene 
• 98-86-2 acetophenone 
• 59239-04-2 1-phenyl-4-penten-1-one oxime 
• 613-91-2 acetophenone oxime 
• 109787-95-3 1-phenyl-1-oxo-3-hydroxypent-4-ene 

Downstream Products

• 106272-35-9 ethyl (E)-3-(3-phenyl-isoxazolin-5-yl)acrylate 
• 1241681-13-9 1-amino-1-phenylpentan-3-ol 
• 6501-72-0 (S,R)-3-phenyl-4,5-dihydro-5-isoxasoleacetic acid 
• 89543-99-7 threo-5'-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylisoxazoline 
• 89543-99-7 erythro-5'-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylisoxazoline 
• 89543-87-3 1-(3-phenyl-isoxazolin-5-yl)ethane-1,2-diol 
• 98-86-2 acetophenone 
• 107-02-8 acrolein 

Relevant academic research and scientific papers

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

Enantio- And Chemoselective Intramolecular Iridium-Catalyzed O-Allylation of Oximes

A method for the enantio- and chemoselective iridium-catalyzed O-allylation of oximes is described. Kinetic resolution in an intramolecular setting provides enantioenriched oxime ethers and aliphatic allylic alcohols. The synthetic potential of the products generated with this method is showcased by their elaboration into a series of heterocyclic compounds and the formal synthesis of glycoprotein GP IIb-IIIa receptor antagonist (-)-roxifiban. Preliminary mechanistic experiments and computational data shed light on the remarkable chemoselectivity of the reaction.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Anionic domino C-O-heterocyclization approach for the synthesis of 5-vinyl isoxazolines

5-Vinyl isoxazolines were isolated in high yields through domino nucleophilic addition-anionic C-O-heterocyclization, when allyl organometallics derived from trans-1,4-dihalobutene were reacted with nitrile oxides. Georg Thieme Verlag Stuttgart.