192936-87-1

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 693-02-7 hex-1-yne 

Downstream Products

• 1228005-73-9 C₂₄H₄₀O₂Si 
• 1228005-84-2 C₂₁H₄₀O₃Si 
• 1228005-77-3 C₂₂H₃₆O₂Si 
• 1394295-32-9 C₂₅H₄₀O₃Si 

Relevant academic research and scientific papers

Cycloadditions of siloxy alkynes with 1,2-diazines: From reaction discovery to identification of an antiglycolytic chemotype

Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf= trifluoromethanesulfonyl, TIPS=triisopropylsilyl. Copyright

Synthesis of eight-membered lactones: Intermolecular [6+2] cyclization of amphoteric molecules with siloxy alkynes

That's about the size of it: The title molecules react with siloxy alkynes in the presence of a Bronsted acid to deliver medium-sized lactones through a [6+2] cyclization (see scheme; TIPS=triisopropylsilyl). This process is the first intermolecular synthesis of such lactones and involves a sequence of several selective ring-opening/ring-closing events. Copyright

Silver-catalyzed aldehyde olefination using siloxyalkynes

We describe the development of a silvercatalyzed carbonyl olefination employing electronrich siloxyalkynes. This process constitutes an efficient synthesis of trisubstituted unsaturated esters, and represents an alternative to the widely utilized Horner-Wadsworth-Emmons reaction. Excellent diastereoselectivities are observed for a range of aldehydes using either 1-siloxy-l-propyne or 1-siloxy1-hexyne. This mild catalytic process also enables chemoselective olefination of aldehydes in the presence of either ester or ketone functionality. Furthermore, since no by-products are generated, this catalytic process is perfectly suited for development of sequential reactions that can be carried out in a single flask.

A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates

(Trialkylsilyl)vinylketenes react with lithium ynolates to generate 3-(oxido)dienylketenes, which undergo rapid 6π-electrocyclization. The ultimate products of this benzannulation are highly substituted resorcinol monosilyl ethers, which are formed via a [1,3] carbon to oxygen silyl?group shift. Further transformations of the benzannulation products are described providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems.

Silver-catalyzed hydroamination of siloxy alkynes

(Chemical Equation Presented) New catalytic process: The silver-catalyzed hydroamination of siloxy alkynes with secondary amides furnishes silyl ketene aminals with high efficiency and excellent diastereoselectivity (see scheme), including some that are unavailable by conventional silylation methods. The reaction comprises a fast and reversible silver-alkyne complexation, followed by a rate-determining C-N bond-forming step.

Silver-catalyzed [2 + 2] cycloadditions of siloxy alkynes

We have described the first [2 + 2] cycloadditions of siloxy alkynes with a range of unsaturated carbonyl compounds. The reactions are efficiently promoted by substoichiometric amount of silver trifluoromethanesulfonimide and display excellent regio- and diastereoselectivity combined with a broad substrate scope. Our studies have established unambiguously the stepwise mechanism of this process and provided evidence for a novel role of silver in the catalytic cycle of the reaction, which involves silver-based complexation and activation of siloxy alkyne toward the subsequent 1,4-addition. Copyright