102690-40-4

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 603-35-0 triphenylphosphine 
• 108-95-2 phenol 
• 620-72-4 phenyl 2-bromoacetate 

Downstream Products

• 32443-55-3 ((triphenyl)-λ⁵-phosphanylidene)acetic acid phenyl ester 
• 1376702-19-0 (E)-phenyl 4-hydroxybut-2-enoate 
• 102690-46-0 phenyl buta-2,3-dienoate 

Relevant academic research and scientific papers

DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates

A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides

A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).

Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes

By using catalytic amounts of copper(II), 4-picoline, and dimethylphenylsilylpinacol borane, a series of allenoates were silylated on the β carbon in good to excellent yields and high (E)-selectivity. The mild and efficient silylation method is conducted in water under atmospheric conditions to afford vinylsilanes.

Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile

Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to γ-hydroxy-α,β-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into β-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of α,β-unsaturated carbonyl compounds.

Asymmetric synthesis of 1,3-oxazolidines via intramolecular aza-michael addition by bifunctional organocatalysts

A novel synthetic route to optically active 1,3-oxazolidines via formal [3 + 2] cycloaddition in the presence of cinchonaalkaloid- thiourea-based bifunctional organocatalysts is reported. This protocol gives easy access to a wide range of chiral 1,3- oxazolidines. In addition, the results show that bifunctional organocatalysts can effect the intramolecular aza-Michael addition, leading to the asymmetric synthesis of nitrogencontaining heterocycles.

Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy- α,β-unsaturated thioester via hemiacetal intermediates

We report an asymmetric oxy-Michael addition to a γ-hydroxy-α, β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.

Cycloadditions, 12. - Influence of Aromatic Alkyl Groups on the Intramolecular Diels-Alder Reaction of Aryl Allenecarboxylates and of Allenecarboxanilides

The aryl allenecarboxylates 4a-o and the allenecarboxanilides 9a, b, e, h, and l, which differ from one another only by the number or by the size of the alkyl groups attached to the arene, are synthesized by the ylide method via the appropriately substituted 2-halo-, 2-phosphonio-, and 2-phosphoranylideneacetic acid derivatives (1-->2-->3-->4 and 6-->7-->8-->9, resp.).By refluxing in xylene they are transformed into the tricyclic compounds 5 and 10; the rates and their differences are discussed.

INTRAMOLEKULARE DIELS-ALDER-REAKTION BEI ALLENCARBONSAEURE-ARYLESTERN

By thermolysis aryl allenecarboxylates 6 and 7 undergo the intramolecular Diels-Alder reaction whereby the aromatic nucleus functions as diene.The lactones 8 and 9 are formed.