87071-03-2

Upstream product

• 87071-00-9 1-[(E)-3-(Tetrahydro-pyran-2-yloxy)-propenyl]-cyclohexanol 
• 5686-96-4 1-(3-hydroxyprop-1-yn-1-yl)cyclohexan-1-ol 
• 67-56-1 methanol 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 87070-89-1 1-[(Z)-3-(Tetrahydro-pyran-2-yloxy)-1-trimethylsilanyl-propenyl]-cyclohexanol 

Downstream Products

• 674368-22-0 1-[(E)-3-methoxycarbonyloxy-1-propenyl]cyclohexanol 
• 59906-45-5 1-(1-Hydroxy-allyl)-cyclohexanol 

Relevant academic research and scientific papers

Atom-Transfer Radical Addition of Alcohols to Aliphatic Alkynes

An intermolecular hydrogen bond-promoted atom-transfer radical addition of simple alcohols to aliphatic alkynes is demonstrated here. Through this strategy, a variety of allyl alcohols can be synthesized in high selectivity and yields. Furthermore, this work reveals the relationship between selectivity and the substrate. ?

Synthesis of cyclic N-tosyliminocarbonates by Lewis acid catalyzed allylic substitution of trichloroacetimidates

Allylic trichloroacetimidates bearing a δ-N-tosylcarbamoyloxy group were prepared in two steps from the corresponding diols, and their Bronsted and Lewis acid catalyzed cyclization reactions were investigated. It was found that N-tosylcarbamates derived from secondary and tertiary alcohols bearing alkyl substituents undergo a chemoselective allylic alkylation to give N-tosyliminocarbonates in good isolated yields. In turn, aryl-substituted substrates tend to give oxazolines by abstraction of the carbamate functionality. The cyclization of N-tosylcarbamates derived from secondary alcohols preferentially give trans-iminocarbonates. However, the trans selectivity varied and depended on the substitution pattern, configuration of the substrate, and the catalyst. A high trans selectivity could be achieved from (E) substrates by using TMSOTf as the catalyst. The synthetic utility of iminocarbonates was demonstrated by transforming them into 1,2-diols and cyclic carbonates as well as into N-tosyloxazolidinones by a halide ion-induced rearrangement. Copyright

Palladium-Catalyzed Carbon Dioxide Elimination-Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols

A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.