124287-68-9

Upstream product

• 126269-41-8 (6-Benzyl-cyclohex-1-enyloxy)-trimethyl-silane 
• 142683-20-3 (6-Benzyl-cyclohex-1-enyloxy)-triisopropyl-silane 

Downstream Products

• 1201816-06-9 2-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexanone 
• 1266373-58-3 6-benzyl-3-(3-hydroxypropyl)cyclohex-2-enone 
• 1266373-59-4 6-benzyl-3-(3-hydroxyundecyl)cyclohex-2-enone 
• 1266373-60-7 6-benzyl-3-(3-hydroxy-5-phenylpentyl)cyclohex-2-enone 
• 1415503-69-3 2-benzylcyclohexa-1,5-dien-1-yl 2-chloroacetate 
• 1428940-91-3 C₁₃H₁₄O₂ 
• 1428940-92-4 C₂₅H₂₃O₅P 
• 1428940-93-5 C₁₃H₁₄O 

Relevant academic research and scientific papers

Palladium-catalyzed saegusa-ito oxidation: Synthesis of α,β-Unsaturated carbonyl compounds from trimethylsilyl enol ethers

Palladium-catalyzed Saegusa-Ito oxidation of trimethylsilyl enol ethers is possible using Oxone as a stoichiometric oxidant and sodium hydrogen phosphate as a buffer. Cyclic and acyclic enones as well as α,β-unsaturated aldehydes are obtained in good to excellent yields.

Regioselective Preparation of α,β-Unsaturated Ketones via the Direct Dehydrogenation of Triisopropylsilyl Enol Ethers

Treatment of the triisopropyl enol ethers 1a-h with ceric ammonium nitrate in dimethylformamide at 0 deg C afforded the α,β-unsaturated ketones 2a-h in 63-98percent yield.

Applications of the β-azidonation reaction to organic synthesis. α,β- Enones, conjugate addition, and γ-lactam annulation

The β-azido functionalization reaction provides a mechanistically different enone synthesis that involves treatment of 2 with fluoride anion to effect desilylation and concomitant β-elimination to give 3. Table 1 lists a number of examples of the direct conversion of a TIPS enol ether into the corresponding α,β-enone via a β-azido TIPS enol ether. The β-azido group can be ionized with Me3Al or Me2AlCl and the intermediate enonium ion trapped by a variety of nucleophiles such as an allylstannane, electron-rich aromatics, TMS enol ethers, Et2AlCN, Me2AlCCR, Me4AlLi, and vinylaluminum reagents to give the products listed in Table 2. The diastereoselectivity of the reaction of a 4-substituted enonium ion with indole shows an unusual increase of selectivity with increasing temperature. Reduction of the azide 2 provides access to β-amino TIPS enol ethers 5, which, for example, can be converted into a cinnamide derivative and cyclized via a putative 'ene' process into a γ-lactam.

New Trialkylsilyl Enol Ether Chemistry: New Regiospecific Methodology for the Synthesis of α,β-Unsaturated Cyclic Ketones

Treatment of TIPS enol ethers with PhIO/TMSN3 followed by desilylation/elimination with fluoride ion gives good yields of the α,β-unsaturated ketone.