71096-87-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 127880-72-2 (2S,8aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1,2-diphenyl-1,2,3,5,6,7,8,8a-octahydro-quinoline 
• 127880-73-3 (2S,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1,2-diphenyl-1,2,3,5,6,7,8,8a-octahydro-quinoline 
• 224045-85-6 2-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohex-1-enyl-cyclobutylidene]-propionic acid ethyl ester 
• 180295-42-5 methyl 2-(tert-butyldimethylsilyloxy)-2-(1-cyclohexenyl)cyclopropanecarboxylate 
• 403621-46-5 C₄₀H₅₄O₄Si 

Relevant academic research and scientific papers

Nazarov reactions intercepted by (4 + 3) cycloadditions with oxygen-substituted dienes

The oxyallyl cation intermediate from the Lewis acid mediated Nazarov reaction of an allenyl vinyl ketone was intercepted by acyclic, 2-silyloxy-substituted butadienes by highly regioselective (4 + 3) cycloadditions. Stereoselectivity was often modest, bu

Regioselective Synthesis of α,α-Difluorocyclopentanone Derivatives: Domino Nickel-Catalyzed Difluorocyclopropanation/Ring-Expansion Sequence of Silyl Dienol Ethers

Silyl dienol ethers prepared from α,β-unsaturated ketones underwent nickel-catalyzed difluorocyclopropanation of the electron-rich alkene moiety with trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate. The subsequent vinylcyclopropane-cyclopentene rear

Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity. Copyright

Enantioselective Formal Total Synthesis of (-)-Dysidiolide

(matrix presentd) An enantioselective formal total synthesis of the sesterterpene (-)-dysidiolide 1 beginning with an intermolecular Diels-Alder reaction of the allene ester 3 and the silyloxydiene 10 is reported.

Diels-Alder Reactions of 2-pyrylium Cations of 2H-Pyran-2-one and 2H-1-Benzopyran-2-one Derivatives

The reactions of 6-methyl-2H-pyran-2-one and 2H-1-benzopyran-2-one with the 2-(trialkylsilyl)oxy dienes 6a-d in the presence of tert-butyldimethylsilyl triflate gave the cycloadducts 7a-c and 8a-d regio- and stereoselectively in moderate yields.The ring junction in the cycloadducts is cis.The stereochemistry of 8a-d is discussed in terms of the 1H NMR spectra of the compounds.Similar reactions of 3-(ethoxycarbonyl)-2-pyrones and 3-(alkoxycarbonyl)coumarins with the 2-(trialkylsilyl)oxy dienes 6a-e gave the cycloadducts 14-18 in satisfactory yields.Dehydrogenation of 7c, 8b, and 8c with DDQ in refluxing toluene afforded 23-25, respectively.

REACTION OF CONJUGATED ENONES WITH tert-BUTYLDIMETHYLSILYL TRIFLATE AND INTRAMOLECULAR ANNELATION

Reaction of 2-cyclohexen-1-ones (3a-c) with tert-butyldimethylsilyl triflate and triethylamine gave selectively cross-conjugated dienol ethers (4a-c) except 3-methyl-2-cyclohexen-1-one (3d).Reaction of 6-(5-ethoxycarbonyl-3,3-dimethyl-4-pentenyl-1)-2-cycl