119897-89-1

Upstream product

• 137610-10-7 ((R)-3-tert-Butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-((R)-3-phenyl-4,5-dihydro-isoxazol-5-yl)-methanone 
• 107-18-6 allyl alcohol 
• 698-16-8 benzohydroximoyl chloride 
• 124154-33-2 (3S,4aR,6R)-3,4a,6-Trimethyl-8-((S)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyl)-1-((R)-1-phenyl-ethyl)-hexahydro-3,6-methano-[1,8]naphthyridine-2,7-dione 
• 153391-18-5 (2S,3aS,7aS)-1-((R)-3-Phenyl-4,5-dihydro-isoxazole-5-carbonyl)-octahydro-indole-2-carboxylic acid ethyl ester 
• 265098-27-9 (1S,5R,7R)-10,10-Dimethyl-3-phenyl-4-((R)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one 
• 17647-39-1 (R)-methyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate 
• 932-90-1 Benzaldoxime 
• 2043-21-2 acryloyl-1,3-oxazolidin-2-one 
• 147721-21-9 (S)-3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid 
• 873-67-6 benzonitrile oxide 
• 1569-94-4 (3-phenyl-4,5-dihydro-isoxazol-5-yl)-methanol 
• 4872-58-6 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid 
• 1142349-87-8 C₁₅H₁₅N₃O₂ 

Downstream Products

• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 64984-98-1 4-phenyl-2-oxa-3-aza-bicyclo[3.1.0]hex-3-ene 
• 159974-70-6 (2R,4R)-4-phenyl-1,2,4-butanetriol 
• 160024-47-5 (R)-5-Methoxymethyl-3-phenyl-4,5-dihydro-isoxazole 

Relevant academic research and scientific papers

Catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol utilizing diisopropyl tartrate as a chiral auxiliary

The catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol was achieved by the use of a catalytic amount of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (R)-2-isoxazolines with high enantioselectivity. In order to realize reproducible higher stereoselection, the addition of a small amount of ethereal compound such as 1,4-dioxane was crucial.

Enantioselective Synthesis of 2-Isoxazolines via Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxide to Achiral Allyl Alcohol

The asymmetric 1,3-dipolar cycloaddition of a nitrile oxide to an achiral allyl alcohol was achieved by the use of (R,R)-diisopropyl tartrate as a chiral auxiliary.Treatment of the allyl alcohol with diethylzinc and the tartrate, followed by the addition

Asymmetric 1,3-dipolar cycloaddition reactions of benzonitrile oxide mediated by a chiral Lewis acid

In this paper we report on the asymmetric 1,3-dipolar cycloaddition reactions of nitrile oxides mediated by pybox/ytterbium triflates, -/magnesium bromide, and -/magnesium perchlorate. It was confirmed that the reactions proceed smoothly to give isoxazoli

Kinetic resolution of 5-(hydroxymethyl)-3-phenyl-2-isoxazoline by using the 'low-temperature method' with porous ceramic-immobilized lipase

A significant enhancement of the enantioselectivity (E value = 249) in the lipase-catalyzed resolution of a primary alcohol, racemic 5-(hydroxymethyl)-3- phenyl-2-isoxazoline (±)-1, was obtained by using the 'low-temperature method' (-60°C) with porous ceramic-immobilized lipase (Amano PS-C II) and vinyl acetate in acetone.

Mechanistic Insights into the Racemization of Fused Cyclopropyl Isoxazolines

Experimental and computational studies of the unexpected racemization of enantiopure fused cyclopropyl isoxazolines are reported. These studies offer insights into the mechanism of racemization, quantify the position of the transition state on the dipolar

Molecular sieve 4 ? generates nitrile oxides from hydroximoyl chlorides. Development of catalyzed enantioselective nitrile oxide cycloadditions to monosubstituted alkenes

The effective generation of nitrile oxide 1,3-dipoles from hydroximoyl chlorides can be achieved with powdered molecular sieves 3 ? and 4 ? as mild solid bases. Rate of nitrile oxide generation depends upon the choice of reaction solvents, among which alc

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones from chiral O-acylmandelamides or lactamides

(-)-O-Acyllactamides or mandelamides in the presence of TBSOTf underwent cyclization reaction to give optically active 2-oxy-1,3-oxazolidin-4-ones, a novel nitrogen analog of orthoesters, in good yields. An X-ray analysis and NOE studies indicated that the absolute configuration at the newly formed chiral carbon was S. For their synthetic application, the 1,3-dipolar cycloaddition of nitrile oxide was examined. The cycloadducts were obtained in a stereoselective manner. Subsequent treatment of the adduct with TBAF resulted in the one-step removal of mandelamide, giving optically active 4,5-dihydroisoxazole and mandelamide in good yields.

Asymmetric 1,3-dipolar cycloaddition of nitrile oxides generated in situ by direct oxidation of aldoximes

The asymmetric 1,3-dipolar cycloaddition of nitrile oxides, generated in situ from aldoximes by direct oxidation with tert-butyl hypochlorite, to 2-propen-1-ol was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (R)-2-isoxazolines with high enantioselectivity up to 96% ee.

Regio- and stereoselective synthesis of isoxazolines via cycloaddition reactions using pregnenolone as chiral auxiliary

The asymmetric 1,3-dipolar cycloaddition reaction of nitrile oxides 2a-b to olefins 1a-c has been acccomplished by employing pregnenolone as chiral auxiliary. The optically pure 3-aryl-5-isoxazoline esters 9 are obtained from the major diastereomer in good yield.

Diastereoselective [3+2] cycloadditions of a camphor-derived chiral N- acryloylhydrazide with nitrile oxides: The preparation of optically pure δ2-isoxazolines

Reaction of a novel chiral N-acryloylhydrazide with various nitrile oxides proceeded smoothly to afford the cycloadduct with high diastereoselectivity (99:1). The auxiliary can be easily removed from the cycloadducts under mild conditions. (C) 2000 Elsevier Science Ltd.