98746-87-3

Upstream product

• 107-18-6 allyl alcohol 
• 536-74-3 phenylacetylene 
• 123-73-9 trans-Crotonaldehyde 
• 100-44-7 benzyl chloride 
• 244176-69-0 (E)-1-phenyl-3-penten-2-one oxime 
• 100-39-0 benzyl bromide 
• 67-56-1 methanol 
• 82456-37-9 1-phenylpent-4-en-2-one 
• 64-17-5 ethanol 
• 70-55-3 toluene-4-sulfonamide 
• 244176-53-2 3-benzyl-5-bromomethylisoxazoline 
• 100-52-7 benzaldehyde 
• 201230-82-2 carbon monoxide 
• 24850-33-7 allyltributylstanane 

Relevant academic research and scientific papers

Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).

Nazarov cyclization of divinyl ketones bearing an ester group at the β-position: A remarkable effect of α-substitution and alkene geometry on regioselectivity

The Nazarov cyclization of divinyl ketones with an ester at the β-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the subtle substitution patterns at the α-position and alkene geometry of α,β and mostly, this selectivity is regardless of substitutions at α′- and β′-positions. The major implications of these observations are an aromatic group at the α-position with E-olefin geometry provides a cyclopentenone in which the double bond is not in conjugation with an ester, whereas Z-olefin provides a cyclopentenone in which the double bond is in conjugation with an ester; and divinyl ketones bearing an ester group at the β-position and an alkyl group at the α-position with E-olefin geometry provide a cyclopentenone in which the double bond is in conjugation with the ester.

Carbonylative Stille coupling reactions of benzyl chlorides with allyltributylstannane catalyzed by palladium nanoparticles

The carbonylative Stille coupling reaction of benzyl chlorides with allyltributylstannane was successfully conducted by using palladium nanoparticles as the catalyst under phosphine ligand-free conditions. The corresponding α,β-unsaturated ketone products

A mild isomerization reaction for β,γ-unsaturated ketone to α,β-unsaturated ketone

A series of β,γ-unsaturated ketones were isomerized to their corresponding α,β-unsaturated ketones by the introduction of DABCO in iPrOH at room temperature. The endo-cyclic double bond (β,γ- position) on ketone was rearranged to exo-cyclic double bond (α,β-position) under the reaction conditions.

Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of βγ,-Unsaturated Ketones

A reaction mixture of β,γ-unsaturated ketone and BF 3·OEt2 in CH3OH was stirred at room temperature and β-methoxy ketone was produced in high yield. The β-amino ketone was obtained as the major product from a reaction mixture of β,γ-unsaturated ketone, AlCl3 and Ts-NH2 in CH2Cl2 at room temperature. This Lewis acid promoted β-substitution reaction mechanism was proposed as that the process occurred via in situ isomerization of β,γ-unsaturated ketone to α,β-unsaturated ketone followed by the 1,4-addition reaction.

Ring opening of 5-(bromomethyl)-2-isoxazolines with magnesium metal in absolute MeOH

Ring opening of 5-(bromomethyl)- and 5-(phenylsulfonylmethyl)-2- isoxazolines with magnesium in absolute methanol at -23 °C and room temperature afforded regiospecifically β,γ-enoximes and (E)-α,β-enoximes, respectively.

A novel stereoselective reaction cascade leading from α-silylated allylic alcohols to aldol-type products

The treatment of α-silylated allylic alcohols with epoxidizing reagents afforded in a highly stereocontrolled fashion α-silylated aldols. The transformation is proposed to proceed either by a reaction cascade involving stereospecific epoxidation of the al

Carbon-carbon bond forming reactions of η3-allyl iron tricarbonyl anions with carbon electrophiles

Reaction of the η3-allyl iron tricarbonyl anion, 1, with alkyl halides (RX, R = -CH3, -CH2Ph, -(CH2)3CH3, -CH(CH3)2,-CH2CH=CH2) followed by treat

ALLYLIC 1,3-REARRANGEMENT OF 1-ALKOXYALLYLPHOSPHONIUM SALTS. REGIOCHEMISTRY OF REACTION OF 1-ALKOXY-2-ALKENYLENEPHOSPHORANES WITH ALDEHYDES

It was found that 1-alkoxyallylphosphonium salts underwent allylic 1,3-rearrangement to afford 3-alkoxyallylphosphonium salts.Reaction of 1-alkoxy-2-alkenylene-phosphoranes with aldehydes gave α-adducts, whereas the reaction in the presence of TMSOTf gave γ-adducts.