25209-35-2

Upstream product

• 859056-54-5 2-methylallyl 2,2-diphenylacetate 
• 117-34-0 2,2-diphenylacetic acid 
• 563-47-3 3-Chloro-2-methylpropene 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 3469-00-9 methyl 2,2-diphenylacetate 
• 107556-97-8 methyl 2,2-diphenyl-4-methyl-4-pentenoate 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 109394-96-9 α,α-diphenyl-γ-methyl-γ,δ-pentenoic acid 
• 25209-47-6 2-isobutyl-2-phenyl phenylacetic acid 
• 137415-98-6 5-bromomethyl-5-methyl-3,3-diphenyl-dihydro-furan-2-one 
• 103825-99-6 3-methyl-5,5-diphenyl-cyclopent-2-enone 
• 155934-15-9 methyl 4-methyl-2,2-diphenylpent-4-en-1-ol 

Relevant academic research and scientific papers

mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives

A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.

Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates for the Synthesis of Sulfonylated Pyrrolidones

A copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones is described. This reaction features good functional group tolerance and wide substrate scope, providing an efficient and straightforward protocol to access this kind of pyrrolidones. Moreover, preliminary mechanistic investigations disclosed that a free-radical pathway might be invovled in the process.

Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations

An expansion of methodologies aimed at the formation of versatile organonitriles, via the intramolecular aminocyanation of unactivated alkenes, is herein reported. Importantly, the need for a rigid tether in these reactions has been obviated. The ease-of-synthesis and viability of substrates bearing flexible backbones has permitted for diastereoselective variants as well. We demonstrated the utility of this methodology with the formation of pyrrolidones, piperidinones, isoindolinones, and sultams. Furthermore, subsequent transformation of these motifs into medicinally relevant molecules is also demonstrated. A double crossover 13C-labeling experiment is consistent with a fully intramolecular cyclization mechanism. Deuterium labeling experiments support a mechanism involving syn-addition across the alkene.

Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO?(SO2)

In the present work, an asymmetric copper-catalyzed radical multi-component cascade reaction of an unsaturated carboxylic acid, aryldiazonium tetrafluoroborate, and DABCO?(SO2)2 (DABSO) has been developed for the enantioselective synthesis of sulfonyl lactones. In this reaction, this SO2 surrogate, DABSO was applied for the first time in the construction of chiral compounds. This multiple-step asymmetric radical reaction was carried out under mild conditions and tolerated a wide range of substrates, resulting in the corresponding sulfonyl lactones with up to 95% chemical yields and 88% ee. The current reaction enriches the research contents of DABSO, and provides a new and efficient strategy to chiral functionalized lactones bearing quarternary stereogenic center. (Figure presented.).

Niobium-Catalyzed Intramolecular Addition of O-H and N-H Bonds to Alkenes: A Tool for Hydrofunctionalization

A convenient, versatile, and easy to handle intramolecular hydrofunctionalization of alkenes (C-O and C-N bonds formation) is reported using a novel niobium-based catalytic system. This atom economic and eco-friendly methodology provides an additional synthetic tool for the straightforward formation of valuable building blocks enabling molecular complexity. Various pyran, furan, pyrrolidine, piperidine, lactone, and lactam derivatives as well as spirocyclic compounds are produced in high yields and selectivities.

Direct oxidative lactonization of alkenoic acids mediated solely by NaIO4: Beyond a simple oxidant

Triflic acid-catalyzed direct oxidative lactonization of alkenoic acids mediated solely by NaIO4 without halogen salts is described. Sodium periodate works not only as an oxidant, but also as an active reagent and directly mediates the lactonization. A new cheap, green, and practical oxidative lactonization approach has been developed using NaIO4 as the sole reagent.

Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines

A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate sco

CuX2-mediated oxybromination/aminochlorination of unsaturated amides: Synthesis of iminolactones and lactams

We report herein a CuX2-mediated halocyclization of γ,δ-unsaturated amides for the synthesis of functionalized iminolactones and lactams respectively under mild reaction conditions. Mechanism studies indicated that N-attack cyclization was via a radical route while oxycyclization was via a nucleophilic attack on the activated CC bond.

FUSED FURAN CONSTRUCTION VIA AN INTRAMOLECULAR CYCLOADDITION REACTION: SYNTHESES OF 4H-CYCLOHEPTA- AND 4H-CYCLOPENTAFURANS

General and efficient syntheses of 4H-cyclohepta- and 4H-cyclopentafurans (4 and 5) have been accomplished employing the intramolecular dipolar cycloaddition based fused furan construction strategy.Treatment of the oximes (20 and 29), readily pre

5-(1-(IMIDAZOL)METHYL)-3,3-DISUBSTITUTED-2(3H)FURANONE DERIVATIVES

Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: STR1 wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring;R 1 and R 2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C. sub.3-C 6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy;R. sub.3, R 4 and R 5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R 4 and R. sub.5 or R 3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R 1 and R 2 substituted benzyl or phenyl.R 6 in the dihydrofuranone series is hydrogen or lower alkyl.Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds. The compounds are particularly useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.