89543-87-3

Upstream product

• 98-86-2 acetophenone 
• 59239-04-2 1-phenyl-4-penten-1-one oxime 
• 109787-95-3 1-phenyl-1-oxo-3-hydroxypent-4-ene 
• 613-91-2 acetophenone oxime 
• 873-67-6 benzonitrile oxide 
• 119496-13-8 5-[1-(tert-Butyl-dimethyl-silanyloxy)-2,2-bis-tert-butylsulfanyl-ethyl]-3-phenyl-4,5-dihydro-isoxazole 
• 119496-37-6 (tert-Butyl-dimethyl-silanyloxy)-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-acetaldehyde 
• 92287-44-0 3-phenyl-5-vinyl-4,5-dihydroisoxazole 
• 89543-89-5 1-(3-Phenyl-4,5-dihydro-isoxazol-5-yl)-2-trityloxy-ethanol 
• 497-06-3 3,4-butenediol 

Downstream Products

• 89543-99-7 erythro-5'-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylisoxazoline 
• 89543-99-7 threo-5'-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylisoxazoline 

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.

DIASTEREOSELECTIVE NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALLYL ETHERS DERIVED FROM 1,1-DITHIO-3-BUTEN-2-OLS.

Highly diastereoselective cycloaddition of nitrile oxides to the title compounds gives masked polyfunctional products amenable to a variety of synthetic elaboration; an entry to enantiomerically pure derivatives is described.

Stereoselective Osmylation of 5-Vinyl-4,5-dihydroisoxazoles

Osmium tetroxide-catalysed cis-hydroxylation of 5-vinyl-4,5-dihydroisoxazoles proceeds stereoselectively affording the anti-products in fair to excellent diastereoisomeric excess; an entry to optically active compounds is also described.

ASYMMETRIC INDUCTION IN NITRILE OXIDE CYCLOADDITIONS TO 3-BUTENE-1,2-DIOL AND DERIVATIVES

Nitrile oxide cycloadditions to 3-butene-1,2-diol and derivatives thereof show varying degrees of erythro selectivity, ranging from 0 to ca. 0.9 kcal/mol.Some of these results arerationalized qualitatively on the basis of the Felkin-Anh-Houk model.