5070-90-6

Upstream product

• 59986-22-0 1,2-dicyclohexyl-ethanol 
• 2550-36-9 Cyclohexylmethyl bromide 
• 931-48-6 2-cyclohexylacetylene 
• 626-62-0 Cyclohexyl iodide 
• 3483-39-4 Cyclohexyloxirane 
• 87100-15-0 cyclohexylboronic acid pinacol ester 
• 56077-28-2 Bromomethyl cyclohexyl ketone 
• 823-76-7 Cyclohexyl methyl ketone 
• 695-12-5 vinylcyclohexane 
• 94594-91-9 acrylcamphorsultam 
• 2043-61-0 cyclohexanecarbaldehyde 
• 78606-84-5 C₂₀H₄₂O₂SSi₂ 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 110-82-7 cyclohexane 

Downstream Products

• 62371-39-5 1,2-dicyclohexylacetylene 

Relevant academic research and scientific papers

Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.

Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes

We have developed a method for stereospecific synthesis of E-alkenes from terminal alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov selectivity. We demonstrate the broad scope of the reaction, which can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines, and a wide range of nitrogen-containing heteroaromatic compounds. Mechanistic studies provide evidence that the copper catalyst activates the alkyne by hydrocupration, which controls both the regio- and diastereoselectivity of the overall reaction. The nickel catalyst activates the alkyl iodide and promotes cross coupling with the alkenyl copper intermediate.

Iterative synthesis of alkenes by insertion of lithiated epoxides into boronic esters

The insertion of lithiated epoxides into boronic esters followed by thermal syn-elimination provides a stereospecific entry to alkenes. This process avoids transition metals and is amenable to iteration to provide higher substitution patterns.

Diastereoselective ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols

(Chemical Equation Presented) Sequential catalysis has evolved as a powerful concept within the past years and allows the more efficient use of catalytically active expensive transition metals in organic synthesis. In this paper we present the stereoselective cross-metathesis-dihydroxylation of various olefins with chiral auxiliary substituted acrylamides. The chiral information (i.e., the auxiliary) introduced in the metathesis reactions allows for a stereoselective subsequent RuO4-catalyzed dihydroxylation. The sequence is concluded by an unusual kinetic resolution of the diastereomeric diols obtained in the oxidation reaction. As a consequence a variety of structurally diverse enantiomerically enriched diols are obtained. To the best of our knowledge the results summarized in this paper represent the first highly efficient diastereoselective RuO4-catalyzed oxidation.

Stereoselectivity of the Thermally Initiated Free-Radical Chain Addition of Cyclohexane to 1-Alkynes

Alkanes can be added to alkynes in a thermally initiated free-radical chain reaction ("ane reaction").The addition of cyclohexane to 1-alkynes 1a-l yields a mixture of (Z)- and (E)-2-cyclohexyl-1-alkenes 3a-l.An essential step in this reaction is the addi

Stereoselective Synthesis of Unhindered Olefins by 2-Fold Extrusion Reactions

Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins.An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2.Stereospecific extrusion of nitrogen yields the cis-thiirane which upon treatment with triphenylphosphine affords the corresponding Z-alkene in good yields.

REACTION OF α,α'-BISSULFIDES WITH LOW VALENT TITANIUM REAGENTS

We have shown that low valent titanium reagents reductively couple α,α'-bis-(trimethylsiloxy) sulfides giving olefines in good yield.With unsymmetrical 1, mixed olefins are obtained suggesting an intermolecular pathway.Finally, we have demonstrated that trans-episulfide 3 is quantitatively converted to trans-stilbene.