124154-34-3

Upstream product

• 17647-39-1 3-phenyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester 
• 144631-72-1 C₄₄H₅₃NO₈Si 
• 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-((S)-1-phenyl-ethyl)-hexahydro-3,6-methano-[1,8]naphthyridine-2,7-dione 
• 272442-18-9 (S)-5-Methoxymethyl-3-phenyl-4,5-dihydro-isoxazole 
• 147721-21-9 (S)-3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid 
• 50899-14-4 (S)-ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate 
• 932-90-1 Benzaldoxime 
• 108-05-4 vinyl acetate 
• 1569-94-4 (3-phenyl-4,5-dihydro-isoxazol-5-yl)-methanol 
• 123-20-6 vinyl n-butyrate 
• 54519-07-2 vinyl ester of 3-phenylpropionic acid 
• 2043-21-2 acryloyl-1,3-oxazolidin-2-one 

Downstream Products

• 159974-67-1 (S)-3,4-dihydroxy-1-phenylbutan-1-one 
• 159974-69-3 (2S,4R)-4-phenyl-1,2,4-butanetriol 

Relevant academic research and scientific papers

Enantioselective Synthesis of Isoxazoline N-Oxides via Pd-Catalyzed Asymmetric Allylic Cycloaddition of Nitro-Containing Allylic Carbonates

A useful method for the enantioselective preparation of isoxazoline N-oxides via Pd-catalyzed asymmetric allylic cycloaddition of nitro-containing allylic carbonates has been developed. By using palladium complex in situ generated from Pd2(dba)3·CHCl3 and phosphoramidite L2 as a catalyst under mild conditions, the transformation afforded vinylated isoxazoline N-oxides in high yields with acceptably high enantioselectivities.

Asymmetric 1,3-dipolar cycloaddition reactions of nitrile oxides catalyzed by chiral binaphthyldiimine-Ni(II) complexes

Asymmetric cycloaddition reactions between several nitrile oxides and 3-(2-alkenoyl)-2-oxazolidinones and 2-(2-alkenoyl)-3-pyrazolidinone derivatives were carried out in the presence of chiral binaphthyldiimine (BINIM)-Ni(II) complexes as catalysts. Using (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complex (30 mol %), good regioselectivity (4-Me/5-Me = 85:15) along with high enantioselectivity (96% ee) of the 4-Me adduct were obtained for the reaction between isolable 2,4,6-trimethylbenzonitrile oxide and 3-crotonoyl-5,5-dimethyl-2-oxazolidinone. Substituted and unsubstituted benzonitrile oxides and aliphatic nitrile oxides, which were generated from the corresponding hydroximoyl chloride in the presence of MS 4A, were reacted with 3-crotonoyl-5,5-dimethyl-2-oxazolidinone, 5,5-dimethyl-3-(2-pentenoyl)-2-oxazolidinone, 5,5-dimethy-3-[3-(ethoxycarbonyl) propenoyl]-2-oxazolidinone, 1-benzyl-2-crotonoyl-5,5-dimethyl-3-pyrazolidinone, and 1-ben-zyl-2-[3-(ethoxycarbonyl)propenoyl]-5,5-dimethy-3-pyrazolidinone in the presence of (K)-BENM-4Ph-2QN-Ni(II) or (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complexes (10-30 mol %) as catalysts to give the corresponding cycloadducts in high yields, with high regioselectively (4-R/5-R = 85:15-99:1) and with moderate to high enantioselectivities (42-95% ee) of the 4-R adducts. Higher enantioselectivities and regioselectivities were obtained for the reactions using pyrazolidinone derivatives as the dipolarophiles. For the cycloadditions of 2-(2-alkenoyl)-1-benzyl-5,5-dimethyl-3-pyrazolidinones catalyzed by (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complex (30 mol %), the enantioselectivity varied from 75% to 95% ee. The reactions between several nitrile oxides and 2-acryloyl-1-benzyl-5,5-dimethyl-3-pyrazolidinone in the presence of (R)-BINIM-4(3,5-xylyl)-2QN-Ni(II) complex (10 mol %) resulted in enantioselectivities (79-91% ee) that exceed those of previously reported enantioselective cycloadditions of acrylic acid derivatives. Furthermore, studies using a molecular modeling program using PM3 calculations were carried out to gain insight into the mechanisms of the asymmetric induction. 2009 American Chemical Society.

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.

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.

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.

Resolution of Δ2-Isoxazoline-5-carboxylates by a Protease from Aspergillus Oryzae Providing Masked Synthons for Enantiopure β-Aminoalcohols and Related Structures

A series of racemic Δ2-isoxazolinecarboxylates have been synthesized and subjected to enzymatic hydrolysis by a protease from Aspergillus oryzae in a two-phase system.Out of these compounds only isoxazoline-5-carboxylates unsubstituted at C-4 w

Synthesis of a bifunctional 2,4-dihydroxy five-carbon synthon. Enantiomerically pure Δ2-isoxazolines by chromatographic resolution

Chromatography on cellulose triacetate allows the separation of (R)- and (S)-4,5-dihydro-3-phenyl-5-isoxazolemethanol in 100% ee. Reductive ring cleavage, diastereoselective reduction of the 3-hydroxy ketones thus obtained, and oxidation of the phenyl rin

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