91897-74-4

Upstream product

• 201230-82-2 carbon monoxide 
• 42599-24-6 E-styryl iodide 
• 66680-84-0 tributyl(propenyl)tin 
• 18415-23-1 1,1-bis(trimethylsilyl)-2-phenylethylene 
• 10487-71-5 crotonyl chloride 
• 143970-73-4 (1E,4Z)-1-phenyl-1,4-hexadien-3-one 1,3-(2,2-dimethyl)propanediyl acetal 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 1342253-39-7 1-hydroxy-1-phenylhex-5-en-3-one 

Downstream Products

• 143970-77-8 trans-2-aza-1-phenyl-2-benzyl-3-methyl-cyclohexanone 
• 960318-70-1 C₂₀H₂₈OSi 
• 143970-77-8 cis-2-aza-1-phenyl-2-benzyl-3-methyl-cyclohexanone 
• 1236879-92-7 triisopropyl[(6E,8E)-5-methyl-9-phenyl-4-(p-toluenesulfonyl)-4-azanona-6,8-dien-1-yn-7-yloxy]silane 
• 1262238-80-1 C₁₅H₁₄N₂O 
• 1008533-96-7 C₂₃H₃₄OSi 

Relevant academic research and scientific papers

Synthesis of cis-2,6-tetrahydropyran-4-one via diastereoselectively intramolecular cyclization of β-hydroxy allyl ketone

A series of cis-2,6-tetrahydropyran-4-ones was synthesized from the intramolecular cyclization reaction of β-hydroxy allyl ketones in the presence of Me3SiOTf as catalyst. The β-hydroxy allyl ketone was prepared from allylation reaction with β-hydroxynitrile without protection of hydroxy functionality under the Barbier-type reaction condition.

Study of the reaction of 1,1-bis(trimethylsilyl)-2-phenylethylene with some acyl chlorides in the presence of AlCl3

1,1-Bis(trimethylsilyl)-2-phenylethylene (1), which has been synthesized from the Peterson reaction between (Me3Si)3CLi and benzaldehyde, reacts with various acyl chlorides (RCOCl, R = Me, Et, iso-Pr, n-Bu, iso-Bu, iso-C5H11, PhCH2, PhCH2CH2) in the presence of AlCl3 to give α-silyl-α,β-unsaturated enones 3a-3h with high E stereoselectivity along with trans-α,β-unsaturated ketones 4a-4h. The enones 3 can be partially converted into the ketones 4 with an excess of AlCl3. Reaction of 1 with RCOCl, (R = Ph, CH3CH=CH) afforded only the ketones 4. Yields were dependent on time and the amounts of AlCl3 used.

Carbometalation of cyclopropenes. Stereoselective synthesis of divinyl ketones via 1,5-hydrogen migration reaction of vinylcyclopropanes

Stereoselective addition of a vinyl cuprate reagent to a cyclopropenone acetal (2) followed by in situ electrophilic trapping with an alkylating agent affords a cis-1-alkyl-2-vinylcyclopropanone acetal (3), which then undergoes thermal 1,5-hydrogen migrat

Carbometalation of Cyclopropenes. Stereoselective Synthesis of Divinyl Ketone Acetals by 1,5-Hydrogen Migration of Vinylcyclopropanes

Stereoselective vinylcupration of a cyclopropenone acetal (1), followed by in situ electrophilic trapping with an alkylating agent, affords via a cis-substituted vinylcyclopropane 2, which stereoselectively rearranges to the acetal of a cross-conjugate di

PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL IODIDES WITH ORGANOSTANNANES: SYNTHESIS OF UNSYMMETRICAL DIVINYL KETONES.

The palladium-catalyzed cross-coupling reaction of vinyl iodides with trimethyl- or tributylvinylstannanes in the presence of carbon monoxide gives unsymmetrical divinyl ketones in good yields. The reaction conditions are neutral and mild enough (40-50 degree C, 15-50 psig carbon monoxide) that other functional groups in either coupling partner can be brought unaltered into the coupled product. The E geometry in both partners is retained in the coupling product, and the Z geometry in the vinyltin reagent is maintained during the coupling reaction, but the coupled product undergoes slow Z to E isomerization under the usual reaction conditions. Isomerization of the divinyl ketone in the reaction medium is slowed in the dark. The reaction rate is especially sensitive to substituents on the vinyltin reagent, probably as a result of steric hindrance in the transmetalation step of the catalytic cycle.