75143-76-9

Upstream product

• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 587-04-2 m-Chlorobenzaldehyde 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 123-54-6 acetylacetone 

Downstream Products

• 1205553-72-5 (S)-5-(2-(3-chlorophenyl)-3-nitropropyl)-3-methyl-4-nitroisoxazole 
• 1448590-05-3 C₂₄H₂₀ClN₂O₃P 
• 86453-97-6 5-[1,2-Dibromo-2-(3-chloro-phenyl)-ethyl]-3-methyl-4-nitro-isoxazole 
• 1459161-40-0 tert-butyl (2S)-2-((1R)-1-(3-chlorophenyl)-2-(3-methyl-4-nitroisoxazol-5-yl)ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1334145-68-4 (S)-5-(2-(3-chlorophenyl)-2-(phenylthio)ethyl)-3-methyl-4-nitroisoxazole 
• 132894-40-7 3-(3-chlorophenyl)-4-(3-methyl-4-nitroisoxazol-5-yl)butanoic acid 
• 132869-29-5 5,6,7,8-tetrahydro-7-(3-chlorophenyl)-3-methyisoxazolo<4,5-b>azepin-5(4H)-one 
• 132894-38-3 ethyl 2-carbethoxy-3-(3-chlorophenyl)-4-(3-methyl-4-nitroisoxazol-5-yl)butyrate 
• 1866-38-2 m-Chlorocinnamic acid 

Relevant academic research and scientific papers

Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes

A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.

Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl- isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25:1 dr and 96% ee).

Trifluoromethylation of aromatic isoxazoles: Regio- and diastereoselective route to 5-trifluoromethyl-2-isoxazolines

It all adds up: The activation of aromatic isoxazoles with a nitro group at the 4-position has enabled the first regio- and diastereoselective trifluoromethylation at the 5-position of isoxazoles by nucleophilic addition using Me3SiCF3 (see scheme; DMF=N,N′- dimethylformamide). The process was demonstrated with a broad range of 3,5-aromatic, heteroaromatic and aliphatic substrates.

Catalytic asymmetric conjugate addition of nitroalkanes to 4-nitro5-styrylisoxazoles

(Chemical equation presented) Nitro versus nitro: 4-Nitro-5- styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol% of a readily prepared phasetransfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).