80522-46-9

Upstream product

• 930-68-7 cyclohexenone 
• 6485-79-6 chlorotriisopropylsilane 
• 13154-24-0 triisopropylsilyl chloride 
• 108-94-1 cyclohexanone 
• 213339-58-3 C₁₁H₂₁F₆NO₄S₂Si 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 67535-64-2 2-(Perfluoroisopropyl)cyclohexanone 
• 135067-08-2 2-Perfluoroisopropyl-1-triisopropylsiloxy-1-cyclohexene 
• 135067-07-1 6-Perfluoroisopropyl-1-triisopropylsiloxy-1-cyclohexene 
• 144810-05-9 Triisopropyl-(2-phenylsulfanyl-cyclohex-1-enyloxy)-silane 
• 144810-06-0 Triisopropyl-(6-phenylsulfanyl-cyclohex-1-enyloxy)-silane 
• 145147-18-8 C-(2-Triisopropylsilanyloxy-cyclohex-2-enyl)-methylamine 
• 1517-01-7 2-azidocyclohexan-1-one 
• 94017-70-6 2-Triisopropylsilanyl-cyclohexanone 
• 137897-38-2 (3-Azido-cyclohex-1-enyloxy)-triisopropyl-silane 
• 13161-18-7 2-(hydroxyphenylmethyl)cyclohexan-1-one 

Relevant academic research and scientific papers

One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes

Regiocontrolled synthesis of precursors for strained cyclohexynes and 1,2-cyclohexadienes is described based on one-pot rearrangement of silyl enol ether followed by formation of enol triflate. Treatment of silyl enol ether with a combination of LDA and tBuOK led to the migration of the silyl group to generate α-silyl enolate, which was treated with Comins' reagent to provide the corresponding enol triflate. The transient α-silylated lithium enolate was smoothly isomerized in the presence of stoichiometric amount of water within one hour at room temperature, providing precursors for cyclohexynes exclusively in one pot. Effects of silyl groups, isomerization of the lithium enolate, and regiocontrolled generation of these precursors for these strained molecules were also investigated.

METHOD FOR PRODUCING SILYLENOL ETHERS

The present invention provides a method for producing a silyl enol ether compound, which is convenient, has highly broad utility and places a low environmental load (less waste). The present invention relates to a method for producing silyl enol ether compound (3), including reacting ketone or aldehyde compound (1) with allylsilane compound (2) in the presence of a base and 0.00001 to 0.5 equivalents of an acid catalyst relative to ketone or aldehyde compound (1), wherein R1 is a hydrogen atom, an alkyl group, an aryl group or the like; R2 and R3 are each a hydrogen atom, a halogen atom, an alkyl group, an aryl group or the like; R1 and R3, R1 and R2, or R2 and R3 optionally form a ring, together with the carbon atom(s) bonded thereto; R4 , R5 and R6 are each a hydrogen atom, an alkyl group or the like; two of R4, R5 and R6 optionally form a ring; R7, R8, R9, R10 and R11 are each a hydrogen atom, an alkyl group or the like; two of R7, R8, R9, R10 and R11 optionally form a ring.

Catalytic [3+2] annulation of aminocyclopropanes for the enantiospecific synthesis of cyclopentylamines

With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yields. Polysubstituted cyclopentylamines, which are often present in bioactive compounds, were obtained with high diastereoselectivity and enantiospecificity. Copyright

Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones

Asymmetric transfer hydrogenation of cyclic and acyclic α,β-unsaturated ketones catalysed by η6-p-cymene/ ruthenium(II) and η5-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic α,β-unsaturated ketones appeared to be more suitable substrates for the synthesis of enantiomerically pure allylic alcohols than do acyclic α,β-unsaturated ketones. A proposed mechanism for the formation of 4-phenyl-[1,3]-dioxolan-2-one from α-tosyloxy- and halo-substituted acetophenones is discussed. The results of further investigations into the reduction of a range of α- tosyloxyacetophenones and the dynamic kinetic resolution of α-substituted ketones is presented.

Pd(OH)2/C-mediated selective oxidation of silyl enol ethers by tert-butylhydroperoxide, a useful method for the conversion of ketones to α,β-enones or β-Silyloxy-α,β-enones

(Chemical Equation Presented) Pd(OH)2-catalyzed oxidation of silyl enol ethers by t-BuOOH gives either β-silyloxy-α,β-enones or α,β-enones in good yields depending on the base used.

Highly reactive trialkylsilylation reagents derived from bis(trifluoromethanesulfonyl)imide - Silylation of functional groups, alkines and reactive aromatics

The synthesis of trialkylsilyl-bis(trifluormethanesulfonyl)imides 3 is described. Compounds 3 with bulky trialkylsilyl groups 3a,b only exist in the silatautomeric form 3a′,b′ under usual conditions, 3c in the N-trimethylsilyl structure. Despite of the bulky silyl substituents in 3a′,b′ their reactivity is higher than that of trimethylsilyltriflate. Alcohols, carbonyl compounds, nitroalkanes and carboxylic acid esters are silylated in good yields, especially by the more reactive triisopropylsilyl derivative 3b′ in presence of tertiary amines, tert.-Butyl carboxylates and benzylcarboxylates are cleaved. Monosubstituted alkines and electron-rich (hetero) aromatics are carbosilylated in presence of N-ethyl-diisopropylamine.

New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers

Triisopropylsilyl enol ethers react with (TsN)2Se to give α-N-tosylamino derivatives in modest to good yields.In the absence of 1,3-diaxial interactions the N-tosylamino group prefers an axial conformation.The axial N-tosylamino derivatives can be readily transformed into the azabicyclononane skeleton, the core structure of a number of alkaloids.

Hydrosilylation of Enones: Platinum Divinyltetramethyldisiloxane Complex in the Preparation of Triisopropylsilyl and Triphenylsilyl Enol Ethers

Enones are regioselectively converted to triisopropylsilyl and triphenylsilyl enol ethers in high yields using triisopropylsilane or triphenylsilane and platinum divinyltetramethyldisiloxane complex 1 (Karstedt's catalyst).

THE 1,3 OC SILYL REARRANGEMENT OF SILYL ENOL ETHER ANIONS - SYNTHESIS OF α-SILYL KETONES

Silyl enol ethers with sterically hindered silyl groups are transformed into the corresponding α-silyl ketones by treatment with n-butyllithium/potassium tert-butylate.