67262-98-0

Upstream product

• 930-68-7 cyclohexenone 
• 57519-88-7 1,1-dichloro-1-phenyl-2,2,2-trimethyldisilane 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 1145-98-8 1,2-diphenyltetramethyldisilane 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 107932-21-8 2-t-butyl-2-cyclohexen-1-one 
• 768-33-2 phenyldimethylsilyl chloride 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 67-56-1 methanol 

Downstream Products

• 167282-50-0 3-dimethyl(phenyl)silylcyclohexanol 
• 20134-00-3 trans-1,3-di(phenylcarbonyloxy)cyclohexane 
• 106477-96-7 (+/-)-cis-1-Benzoyloxy-cyclohexanol-⁽³⁾ 
• 106477-96-7 (+/-)-trans-1-Benzoyloxy-cyclohexanol-⁽³⁾ 
• 20134-00-3 (1RS,3SR)-cyclohexane-1,3-diyl dibenzoate 
• 244109-56-6 (R)-3-(dimethyl(phenyl)silyl)cyclohexan-1-one 
• 244109-59-9 2-((trimethylsilyl)oxy)-4-(dimethylphenylsilanyl)cyclohexane 
• 244109-48-6 C₁₄H₂₂OSi 
• 244109-47-5 C₁₆H₂₄O₂Si 
• 244109-46-4 C₁₄H₂₂OSi 
• 244109-51-1 C₁₈H₂₈OSi 
• 244109-45-3 (S)-5-(dimethyl(phenyl)silyl)cyclohex-2-enone 
• 913365-68-1 (S)-3-(dimethyl(phenyl)silyl)-cyclohexanone 
• 244109-58-8 (R)-5-(dimethyl(phenyl)silyl)cyclohex-2-enone 

Relevant academic research and scientific papers

Influence of β-Silyl Groups in Cycloalkanones on the Norrish Type I and Type II Cleavages

The Norrish type I cleavage overwhelms the type II cleavage in the photolysis of α-alkylcycloalkanones bearing an SiMe3, SiMe2Ph, SiMePh2, or SiPh3 group at the β-position, of which the quantum yields are often greater than those of the non-silylated cycl

EVIDENCE FOR INTERMIDIATE ?-COMPLEXES IN THE ADDITION OF TRIALKYLSILYL AND TRIALKYLSTANNYLCUPRATES TO α,β-UNSATURATED ENONES

Low temperature 13C NMR spectra of solutions generated during the addition of metallocuprates (PhMe2Si)3CuLi2, PhMe2Si(Me)Cu(CN)Li2, (Me3Sn)3CuLi2 and Mesu

Total Synthesis of Talatisamine

Talatisamine (1) is a member of the C19-diterpenoid alkaloid family, and exhibits K+ channel inhibitory and antiarrhythmic activities. The formidable synthetic challenge that 1 presents is due to its highly oxidized and intricately fused hexacyclic 6/7/5/6/6/5-membered-ring structure (ABCDEF-ring) with 12 contiguous stereocenters. Here we report an efficient synthetic route to 1 by the assembly of two structurally simple fragments, chiral 6/6-membered AE-ring 7 and aromatic 6-membered D-ring 6. AE-ring 7 was constructed from 2-cyclohexenone (8) through fusing an N-ethylpiperidine ring by a double Mannich reaction. After coupling 6 with 7, an oxidative dearomatization/Diels–Alder reaction sequence generated fused pentacycle 4 b. The newly formed 6/6-membered ring system was then stereospecifically reorganized into the 7/5-membered BC-ring of 3 via a Wagner–Meerwein rearrangement. Finally, Hg(OAc)2 induced an oxidative aza-Prins cyclization of 2, thereby forging the remaining 5-membered F-ring. The total synthesis of 1 was thus accomplished by optimizing and orchestrating 33 transformations from 8.

Basic Copper Carbonate-Catalyzed Silyl Conjugate Additions to α,β-Unsaturated Carbonyls in Water

We report here the silylation of α,β-unsaturated acceptors in water at room temperature using a copper catalyst. A broad substrate scope, including chalcone derivatives, esters, nitrile, and dienones, has been explored. In all cases, the reaction proceede

[(18-C-6)K][(NC)CuI-SiMe2Ph], a Potassium Silylcyanocuprate as a Catalyst Model for Silylation Reactions with Silylboranes: Syntheses, Structures, and Catalytic Properties

CuI-catalyzed silylation reactions involving silylboranes (in particular, pinB-SiMe2Ph (1)) as silyl sources have recently gained considerable attention. One of the most efficient and versatile and yet simplest catalyst systems consi

1,3-γ-Silyl-elimination in electron-deficient cationic systems

Placement of an electron-withdrawing trifluoromethyl group (-CF 3) at a putative cationic centre enhances γ-silyl neighbouring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway is 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation. The scope of this cyclopropanation reaction is explored for numerous cyclic and acyclic examples, proving this method to be a viable approach to preparing CF3-substituted cyclopropanes and bicyclic systems, both containing quaternary centres. Rate-constants, kinetic isotope effects, and quantum mechanical calculations provided evidence for this enhancement and further elaborated the disparity in the reaction outcome between these systems and previously studied γ-silyl systems.

CuI-catalyzed conjugate addition of silyl boronic esters: Retracing catalytic cycles using isolated copper and boron enolate intermediates

Copper(I)-catalyzed conjugate additions of silyl boronic esters to α,β-unsaturated aldehydes, ketones, and esters are synthetically well-established reactions. For the first time central reactive intermediates as well as the boron enolates as the primary

Copper(II)-catalyzed silyl conjugate addition to α,β-unsaturated conjugated compounds: Bronsted base-assisted activation of Si-b bond in water

A mild method for the installation of the dimethylphenylsilyl group on the β-carbon of electron-deficient olefins is reported. In the presence of a catalytic amount of copper(II) (1 mol %) and amine base (5 mol %) at rt, the transformation proceeds effici

Metal-free catalytic C-Si bond formation in an aqueous medium. enantioselective NHC-catalyzed silyl conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls

A metal-free method for enantioselective conjugate addition of a dimethylphenylsilyl group to α,β-unsaturated carbonyls is reported. Transformations are catalyzed by a chiral N-heterocyclic carbene (NHC), performed in an aqueous solution (3:1 mixture of water and tetrahydrofuran) and are operationally simpler to perform than the NHC-Cu-catalyzed variant. The chiral catalyst is generated from an enantiomerically pure imidazolinium salt (prepared in three steps) and a common organic amine base (dbu). NHC-catalyzed processes proceed with 5.0-12.5 mol % catalyst loading at 22 °C within 1-12 h, affording the desired β-silyl carbonyls in 85:15 to >98:2 enantiomeric ratio and in 50% to >98% yield. Cyclic enones or lactones and acyclic α,β-unsaturated ketones, esters, and aldehydes can be used as substrates.

Rhodium(I)-catalyzed enantioselective 1,4-addition of nucleophilic silicon

A rhodium(I)-catalyzed activation of a silicon-boron linkage, that is, the transmetalation of silicon from boron to rhodium(I) by means of an RhI-OH complex, enables the conjugate transfer of nucleophilic silicon onto α,β-unsaturated acceptors. Pre- or in situ formed cationic rhodium(I)-binap complexes catalyze this novel carbon-silicon bond formation with exceptional enantiocontrol, 92 to >99% ee for cyclic carbonyl and carboxyl compounds as well as >99% ee for acyclic carboxyl compounds.