74959-16-3

Upstream product

• 74959-12-9 C₁₁H₁₀ClNO₃ 
• 123208-56-0 (E)-3-phenyl-2-propenyl glyoxylate oxime 
• 112654-61-2 (E)-3-phenyl-2-propenyl (nitrooxy)acetate 
• 112654-60-1 (E)-cinnamyl bromoacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 61363-95-9 2-Chloro-3-oxo-butyric acid (E)-3-phenyl-allyl ester 
• 188626-56-4 cinnamyl 2-diazoacetate 

Downstream Products

• 74970-88-0 (4R,5S)-4-Hydroxymethyl-5-phenyl-4,5-dihydro-isoxazole-3-carboxylic acid 

Relevant academic research and scientific papers

Acyclic nitronate olefin cycloaddition (ANOC): regio- And stereospecific synthesis of isoxazolines

We report the first demonstrations of intra- and intermolecular acyclic nitronate olefin cycloaddition (ANOC) reactions that enable the highly efficient syntheses of isoxazolines bearing various functional groups. This general approach to accessing γ-lactone fused isoxazolines was hitherto unprecedented. The room temperature transformations reported herein exhibit wide substrate scopes, as evidenced by more than 70 examples, including the generation of five tricyclic isoxazolines. The robustness of this methodology was confirmed by a series of trials that afforded highly functionalized isoxazolines. Both experimental results and density functional theory calculations indicate that these transformations proceed via the in situ formation of acyclic nitronates together with concerted [3+2] cycloaddition and tert-butyloxy group elimination processes to give regio- and stereospecificity. This journal is

Preparation method of gamma-butyrolactone isoxazoline bicyclic framework compound

The invention relates to a preparation method of a gamma-butyrolactone isoxazoline bicyclic framework compound, which comprises the steps of reacting a diazo compound and a nitrite compound in an organic solvent at temperature of 25-80 DEG C, and completely reacting to obtain the gamma-butyrolactone isoxazoline bicyclic framework compound. The preparation method disclosed by the invention has theadvantages of rich raw material sources, wide reaction substrate universality, simplicity and convenience in operation and the like.

Conversion of Unsaturated Alcohols into Functionalized Tetrahydrofurans and Tetrahydropyrans via Nitrile Oxide Dipolar Cycloadditions

The intramolecular nitrile oxide cycloaddition (INOC) of a series of unsaturated oximino ethers has been investigated.The synthesis of the olefinic nitrile oxides involves treating an unsaturated alcohol with a α-bromoalkanal O-(trimethylsilyl)oxime in the presence of fluoride ion followed by subsequent sodium hypochlorite oxidation.The nitrile oxides were not isolated but spontaneously underwent intramolecular cycloaddition to give fused five- and six-membered ring ethers.The preferred stereoisomer in the formation of the five-membered ring ethers is trans, whereasin the six-membered ring ethers the cis isomer predominates.MM2 calculations help rationalize the observed stereoselectivity.The ratio of diastereomeric products from the INOC reaction appears to correlate with product stabilities.Simple heating of some of the oximino ethers led to intramolecular cycloaddition.The ring closure apparently proceeds subsequent to a tautomeric equilibration of the oxime with a transient nitrone which is trapped by the neighboring ?-bond.

Intramolecular 1,3-Dipolar Cycloadditions of Aliphatic Nitrile Oxides

Treatment of functionalized 1-chloro-oximes (3c and 4a,b) with triethylamine originates nitrile oxides (1c and 2a,b) which undergo an intramolecular cycloaddition providing fused-ring isoxazole derivatives (7c and 8a,b).The latter reaction was not observe