481014-56-6

Upstream product

• 100-51-6 benzyl alcohol 
• 79-03-8 propionyl chloride 
• 78385-36-1 benzyloxycarbonylmethyltriphenylphosphonium bromide 
• 5437-45-6 Benzyl bromoacetate 

Downstream Products

• 1353722-08-3 benzyl 1-benzyl-2-ethyl-4-phenyl-1H-pyrrole-3-carboxylate 
• 1196497-31-0 benzyl 1-cyclohexyl-2-ethyl-4-phenyl-1H-pyrrole-3-carboxylate 
• 1610598-90-7 C₁₄H₁₃F₃N₂O₂ 
• 1610599-04-6 C₁₄H₁₃F₃N₂O₂ 
• 4949-45-5 benzyl 2-methylacetoacetate 

Relevant academic research and scientific papers

PPh3-catalyzed β-selective addition of α-fluoro β-dicarbonyl compounds to allenoates

A highly selective phosphine-catalyzed β-addition of α-fluoro β-dicarbonyl compounds to allenoates has been developed. Both α-fluoro β-diketones and α-fluoro β-keto esters prove to be competent fluorocarbon nucleophiles, giving a series of the β-addition products bearing a fluorinated quaternary carbon center in good to excellent yields and with excellent regioselectivities. A plausible reaction pathway is presented.

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

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

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.