99564-82-6

Upstream product

• 874-23-7 2-acetylcyclohexanone 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 75-77-4 chloro-trimethyl-silane 
• 62269-46-9 1-(2-(trimethylsilyloxy)-1(Z)-cyclohexen-1-yl)-ethanone 

Downstream Products

• 90926-37-7 <2-Oxocyclohexyl>-1.3-butandion 

Relevant academic research and scientific papers

Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes

A Diels-Alder reaction of novel inner-outer-ring 1,3-silyloxydienes 5-8 with a variety of dienophiles to afford highly functionalized polycyclic structures is reported. The inner-outer-ring 1,3-silyloxydienes 5-8 containing five- to seven-membered carbocyclic and heterocyclic rings were prepared in a single reaction vessel from 2-acetylcyclocarbonyls in quantitative yields. The Diels-Alder reaction with 1,4-benzoquinone (BQ), dimethyl acetylenedicarboxylate (DMAD), and methyl vinyl ketone (MVK) proceeded smoothly at room temperature, affording functionalized polycyclic naphthols, phenols, and enones with high regioselectivity and good yields (39-75%). Moreover, dienes 5-8 also reacted in a hetero-Diels-Alder reaction with benzaldehyde (BA) and N-benzylideneaniline (NBA) in the presence of catalytic amounts of ZnCI2, affording substituted polycyclic pyranones and pyridinones in good yields (40-93%). Overall, our synthetic strategy provides straightforward access to an interesting set of polycyclic structures useful for natural and nonnatural product synthesis.

Regioselective synthesis and acylation of cyclic bis-(trimethylsiloxy)- 1,3-dienes - New and versatile 1,3-dianion synthons

Cyclohexanone-derived bis-(trimethylsiloxy)-1,3-dienes were regioselectively prepared by the use of different silylating systems. These dienes represent new and versatile 1,3-dianion synthons in Lewis-acid catalyzed acylation reactions.

Domino reaction of 1,3-bis(trimethylsilyloxy)-1,3-dienes with oxalyl chloride: General and stereoselective synthesis of γ-alkylidenebutenolides

The Lewis acid catalyzed cyclization of oxalyl chloride with 1,3-bis-(trimethylsilyloxy)-1,3-dienes 3, derived from 1,3-dicarbonyl compounds 1, provides a new and general approach for the synthesis of γ-alkylidenebutenolides 4, a pharmacologically and syn

Synthesis of polycyclic structures by Diels-Alder reaction using inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes

In this paper we describe regioselective one-pot preparations of inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes and their Diels-Alder reactions with electron-deficient dienophiles. The dienes were prepared in quantitative yield, and the Diels-Alder reactions proceeded smoothly, regioselectively and with good yields, allowing efficient construction of highly functionalized polycyclic skeletons such as naphthofurans, benzofurans and various carbocycles present in natural and non-natural products.

Utilisation de Me3SiI prepare in situ pour l'obtention de bis(trimethylsiloxy-1,3) diene-1,3

The in situ generation of iodotrimethylsilane, in the presence of triethylamine, is a convenient route to 1,3-bis(trimethylsiloxy)-1,3-diene.

Reactions of Trialkylsilyl Trifluoromethanesulfonates, III. - Synthesis of 1,3-Bis(trimethylsiloxy)-1,3-dienes and 3-Trimethylsiloxy-2-butenoates Silylated in Position 4

Bis(trimethylsiloxy)-1,3-dienes 5a - n are obtained by reaction of 1,3-dicarbonyl compounds 1 with trimethylsilyl trifluoromethanesulfonate (2) in the presence of triethylamine (3).The silyl enol ether 8 is silylated by 2/3 to yield 1,3-bis(trimethylsiloxy)-1,3-butadiene (5o).Depending on the conditions, alkyl 3-oxobutanoates 12 react with 2/3 to give the γ-silylated alkyl 3-trimethylsiloxy-2-butenoates 15 or 16.