80522-47-0

Upstream product

• 94017-66-0 (2S,4S)-4-tert-Butyl-2-triisopropylsilanyl-cyclohexanone 
• 6485-79-6 chlorotriisopropylsilane 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 98-53-3 4-tercbutyl-cyclohexanone 

Downstream Products

• 94017-66-0 (2S,4S)-4-tert-Butyl-2-triisopropylsilanyl-cyclohexanone 
• 94017-66-0 (2S,4R)-4-tert-Butyl-2-triisopropylsilanyl-cyclohexanone 
• 32741-89-2 5-(tert-butyl)azepan-2-one 
• 937-07-5 4-tert-butylcyclohex-2-enone 

Relevant academic research and scientific papers

Intermolecular C-O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds

Due to the high reactivity of alkoxyl (RO·) radicals and their propensity to easily undergo β-scission or Hydrogen Atom Transfer (HAT) reactions, intermolecular alkoxylations involving RO· radicals are barely described. We report herein for the first time the efficient intermolecular trapping of alkoxyl radicals by silyl enol ethers. This photoredox-mediated protocol enables the introduction of both structurally simple and more complex alkoxy groups into a wide range of ketones and amides.

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.

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.

Oxidative addition of azide anion to triisopropylsilyl enol ethers: Synthesis of α-azido ketones and 2-amino(methoxycarbonyl)alk-2-en-1-ones

Treatment of triisopropylsilyl enol ethers with ceric ammonium nitrate/sodium azide at -20°C in acetonitrile gives α-azido ketones in average to good yields (50-80%). Subsequent conversion of the α-azido ketones into 2-amino(methoxycarbonyl)cycloalk-2-en-1-ones is described.

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.

STUDIES WITH TRIALKYLSILYLTRIFLATES: NEW SYNTHESES AND APPLICATIONS

Syntheses and applications are described for three useful reagents for silylation of unreactive substrates, tert-butyldimethylsilyl, triisopropylsilyl, and octadecyldimethylsilyl triflate.