81238-70-2

Upstream product

• 81238-63-3 3,3-dimethyl-6-phenyl-1,2-dioxa-4-cyclohexene 
• 17137-22-3 (E)-4-Methyl-1-phenyl-pent-1-en-3-ol 
• 103-64-0 bromostyrene 
• 14274-07-8 methyl trans-β-benzoylacrylate 
• 36597-09-8 4-methyl-1-phenyl-3-penten-1-one 
• 36597-08-7 (E)-4-methyl-1-phenyl-2-penten-1-one 
• 72486-22-7 4-Methyl-1-phenylpenta-1,3-diene 

Relevant academic research and scientific papers

Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air

A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.

Concise Construction of the Tricyclic Core of Bullataketals Enabled by a Biomimetic Intermolecular (3 + 3) Type Cycloaddition

A remarkable TFA-mediated method for the construction of a biologically interesting tricyclic ketal skeleton was uncovered by starting from a variety of readily available acylphloroglucinol and diacylphloroglucinol substrates. This approach, which mimics a biosynthetic olefin isomerization/hemiacetalization/dehydration/(3 + 3) type cycloaddition sequence through a 2H-furan-1-ium intermediate, establishes a viable synthetic strategy for efficient synthesis of bullataketals' analogs.

PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.

γ-HYDROXYLATION OF ENONES USING TERT-BUTYL HYDROPEROXIDE AND OXYGEN

A free radical hydroxylation of enones using tert-butyl hydroperoxide and oxygen provides γ-hydroxyenones.

PALLADIUM(O) CATALYZED REACTION OF 1,3-DIENE 1,4-EPIPEROXIDES

Reaction of 1,3-diene 1,4-epiperoxides with Pd(PPh3)4 catalyst forms the corresponding 4-hydroxy enones, syn diepoxides, and 1,4-diols as the major products.The results are interpreted as being due to competing Pd(O)/ Pd(II) and Pd(O)/ Pd(I) exchange mechanisms.