21053-63-4

Upstream product

• 34450-61-8 (Z)-3-iodo-but-2-enoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 616-02-4 citraconic acid anhydride 
• 203131-19-5 4-methyl-2-(triisopropyl)silyloxy-furan 
• 66003-76-7 Diphenyliodonium triflate 
• 722-56-5 diphenyliodonium nitrate 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 6124-79-4 4-methyl-2(5H)-furanone 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 74796-61-5 (E)-4-Methyl-5-phenyl-2-trimethylsilanyloxy-pent-3-enenitrile 
• 13910-25-3 3-Methyl-4-phenyl-but-2-enal 
• 99344-38-4 2α-bromo-3β-methyl-4β-phenyl-γ-butyrolactone 

Downstream Products

• 357933-30-3 (4R,5S)-4-methyl-5-phenyldihydrofuran-2(3H)-one 
• 99344-45-3 phenyl-1 methyl-2 butene-2 diol-1,4 

Relevant academic research and scientific papers

Stereoselective preparation of highly functionalized (Z)-3-magnesiated enoates by an iodine - Magnesium exchange reaction

3-Iodoenoates are converted into the corresponding alkenylmagnesium species with complete retention of configuration of the double bond; both direct reaction and copper(I)-mediated reactions with various electrophiles provide polyfunctional enoates.

Kinetic Resolution and Dynamic Kinetic Resolution of γ-Aryl-Substituted Butenolides via Copper-Catalyzed 1,4-Hydroboration

Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of γ-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration using pinacolborane is reported. With a copper-Ph-BPE catalyst, selectivity factors were extremely high (s=>400) with regard to the kinetic resolution of β-methyl-γ-phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched γ-butyrolactones (>99% ee) containing β,γ-substituents. (Figure presented.).

Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts

The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.

Etude d'α-bromo-butyrolactones; application a la preparation du methyl-3 phenyl-4 Δ2 butenolide et du methyl-2 phenyl-1 butene-2 diol-1,4 de configuration Z

Starting from 2,3-dihydrofuranic compounds, we prepare the corresponding α-bromohydrines and α-bromo-butyrolactones.A solvolytic method of equilibration of these bromolactones in DMF is described.All the stereoisomers are separated and studied.With a Cβ s

A SIMPLE ROUTE TO Δ2-BUTENOLIDES FROM CONJUGATED ALDEHYDES

A variety of Δ2-butenolides may be synthesized by oxidation of the O-trimethylsilylcyanohydrins of α,β-unsaturated aldehydes using pyridinium dichromate in dimethylformamide.