5729-66-8

Upstream product

• 3066-75-9 allyl diethyl phosphate 
• 93-55-0 1-phenyl-propan-1-one 
• 1623-19-4 triallyl phosphate 
• 7393-43-3 tetraallyl tin 
• 24850-33-7 allyltributylstanane 
• 24253-30-3 5-hexen-3-one 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 2551-83-9 allyltrimethoxysilane 
• 141-82-2 malonic acid 
• 4436-22-0 (2S,3R)-2-methyl-3-phenyloxirane 
• 762-73-2 trimethyl(allyl)stannane 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 13278-26-7 3-hydroxy-3-phenylpentanoic acid 
• 56422-91-4 (E)-4-phenyl-3-hexen-2-one 

Relevant academic research and scientific papers

Indium-mediated allylation of carbonyl compounds in deep eutectic solvents

This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u

Organocatalytic Trapping of Elusive Carbon Dioxide Based Heterocycles by a Kinetically Controlled Cascade Process

A conceptually novel approach is described for the synthesis of six-membered cyclic carbonates derived from carbon dioxide. The approach utilizes homoallylic precursors that are converted into five-membered cyclic carbonates having a β-positioned alcohol group in one of the ring substituents. The activation of the pendent alcohol group through an N-heterocyclic base allows equilibration towards a thermodynamically disfavored six-membered carbonate analogue that can be trapped by an acylating agent. Various control experiments and computational analysis of this manifold are in line with a process that is primarily dictated by a kinetically controlled acylation step. This cascade process delivers an ample diversity of six-membered cyclic carbonates in excellent yields and chemoselectivities under mild reaction conditions.

Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model

The chelation-control model explains the high diastereoselectivity obtained in additions of organometallic nucleophiles to α-alkoxy ketones but fails for reactions of allylmagnesium halides. Low diastereoselectivity in ethereal solvents results from no chelation-induced rate acceleration. Additions of allylmagnesium bromide to carbonyl compounds are diastereoselective using CH2Cl2 as the solvent even though rate acceleration is still absent. Stereoselectivity likely arises from the predominance of the chelated form in solution. Therefore, a revised chelation-control model is proposed.

Hydroxyl group-assisted palladium-catalyzed lactonization of homoallylic alcohols

A convenient and highly efficient synthesis of α-methylene-γ- lactones through the palladium(II)-catalyzed lactonization of homoallylic alcohols with alkynamides has been reported. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This process provides a route to construct naturally occurring biologically multifunctional α-methylene-γ- lactones. The time has come to.i?lactonize: α-Methylene- γ-lactones are synthesized through the PdII-catalyzed lactonization of homoallylic alcohols with alkynamides. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This provides a route towards naturally occurring biologically multifunctional α-methylene- γ-lactones. Copyright

Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright

Rhodium-catalyzed redox allylation reactions of ketones

Ketones react with allyl acetate to generate tertiary homoallylic alcohols in the presence of a rhodium catalyst and bis(pinacolato)diboron. A range of substrates, including aryl, alkyl and cyclic ketones react smoothly under these conditions. Diastereoselective allylation reactions of functionalized ketones such as pregnenolone acetate are also reported.

Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity.

Mild and efficient barbier allylation reaction mediated by magnesium powder under solvent-free conditions

A novel and highly efficient synthesis of homoallylic alcohols is achieved by the allylation of carbonyl compounds using magnesium powder as mediator under solvent-free conditions. A series of aldehydes and ketones are converted to the corresponding homoa

Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates

A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.