147189-58-0

Upstream product

• 89368-01-4 2-styryloxirane 
• 544-97-8 dimethyl zinc(II) 
• 64252-49-9 (E)-4-Phenyl-2-pentensaeure-methylester 
• 34713-70-7 2-Phenylpropanal 
• 115476-97-6 (E)-ethyl 4-phenylpent-2-enoate 

Downstream Products

• 1259027-52-5 (R)-(E)-2-(bis(4-(dimethylamino)phenyl)methyl)-4-phenylpent-3-enal 
• 1259027-51-4 (2E)-4-phenylpent-2-enal 

Relevant academic research and scientific papers

Stereoselective Organocatalytic Synthesis of α,α-Difluoro-γ,γ-Disubstituted Butenals

A highly stereoselective reaction of α,α-difluoro-γ,γ-disubstituted butenals 2 bearing two different substituents at the γ position has been developed with an organocatalytic system of l-proline (30 mol %) and salicylic acid (60 mol %). This novel reactio

Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates

The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.

Enantioselective α-and γ-alkylation of α,β- unsaturated aldehydes using dienamine activation

The enantioselective alkylation of α,β-unsaturated aldehydes with stabilized carbocations as electrophiles via the activation as dienamine intermediates is described. This unique application of dienamine catalysis allows for the first enantioselective γ-a

Regioselective SN2 opening of vinylic epoxides with trialkylzincates and trialkylaluminates

The use of trialkylorganozincates and tetraalkylaluminates allows regioselective SN2 nucleophilic opening of vinylic epoxides. The reaction occurs with an anti-substitution pattern and can be applied to a wide range of substrates. We also show that the solvent and the structure of the epoxide have an influence on the substitution products' ratio. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus

The diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus are examined. (E)-N-Benzyl-O(4-phenylpent-2-enyl)hydroxylamine rearranges in 30% de to afford

Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc

The mechanism of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc has been studied. Experiments which rule out a π-allyl mechanism were carried out. Trapping carbometalated products and synthesis and successful reaction of alkyl palladium species provided strong evidence in favor of an enantioselective carbopalladation as the key step in the mechanism. The studies also suggest that a cationic palladium species is responsible for carbopalladation of the alkene. The combination of palladium and dialkylzinc is unique in that the dialkylzinc functions both in the transmetalation to palladium and as a Lewis acid in forming the reactive cationic palladium species.

Diastereoselectivity of the thio-Claisen rearrangement of acyclic precursors bearing a chiral centre adjacent to carbon 6

A number of chiral allylic alcohols have been prepared and submitted to a Mitsunobu reaction with dithioacetic acid. Allyl dithioesters were deprotonated by LDA at -30°C and resulting enethiolates were quenched with iodomethane to afford quantitatively S-