1043872-70-3

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1258793-36-0 (R)-tert-butyl 3-(2,2-bis(phenylsulfonyl)ethyl)-3-(4-fluorobenzyl)-2-oxoindoline-1-carboxylate 
• 1609262-06-7 (R)-tert-butyl 3-(4-fluorobenzyl)-3-((S)-2-nitro-1-phenylethyl)-2-oxoindoline-1-carboxylate 
• 1391859-11-2 tert-butyl 3-(1,4-dioxo-1,4-diphenylbutan-2-yl)-3-(4-fluorobenzyl)-2-oxoindoline-1-carboxylate 
• 1229652-64-5 (S)-tert-butyl-3-(4-fluorobenzyl)-3-(hydroxymethyl)-2-oxoindoline-1-carboxylate 

Relevant academic research and scientific papers

Taming Radical Intermediates for the Construction of Enantioenriched Trifluoromethylated Quaternary Carbon Centers

Demonstrated herein is the construction of trifluoromethylated quaternary carbon centers by an asymmetric radical transformation. Enantioenriched trifluoromethylated oxindoles were accessed using a hypervalent iodine-based trifluoromethyl transfer reagent in combination with a magnesium Lewis acid catalyst and PyBOX-type ligands to achieve up to 99 % ee and excellent chemical yields. Mechanistic studies were performed by experimental and computational methods and suggest a single-electron transfer induced SN2-type mechanism. This example is thereby the first report on the construction of enantioenriched trifluoromethylated carbon centers using hypervalent iodine-based reagents proceeding through such a reaction pathway.

Microfluidic Visible-Light Paternò–Büchi Reaction of Oxindole Enol Ethers

A novel microfluidic visible-light process for the functionalisation of oxindoles is reported. The chemistry is based on the reactivity of the corresponding enol ethers, which participate in a site-, regio- and diastereoselective [2+2] heterocycloaddition (Paternò–Büchi) process. The mild reaction conditions, the use of available ketones, together with the high generality (23 examples) and robustness (up to gram scale) make this process a useful synthetic platform for the construction of structurally strained heterocycles.

Polyfunctional Bis-Lewis-Acid-/Bis-Triazolium Catalysts for Stereoselective 1,4-Additions of 2-Oxindoles to Maleimides

Achieving enzyme-like catalytic activity and stereoselectivity without the typically high substrate specificity of enzymes is a challenge in the development of artificial catalysts for asymmetric synthesis. Polyfunctional catalysts are considered to be a promising tool for achieving excellent catalytic efficiency. A polyfunctional catalyst system was developed, which incorporates two Lewis acidic/Br?nsted basic cobalt centers in combination with triazolium moieties that are crucial for high reactivity and excellent stereoselectivity in the direct 1,4-addition of oxindoles to maleimides. The catalyst is assembled through click chemistry and is readily recyclable through precipitation by making use of its charges. Kinetic studies support a cooperative mode of action. Diastereodivergency is achievable with either Boc-protected or unprotected maleimide.