172376-40-8

Upstream product

• 113309-44-7 (3S) methyl 3-hydroxy-3-cyclohexylpropanoate 
• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 214853-88-0 (S)-4-cyclohexyl-oxetan-2-one 
• 2043-61-0 cyclohexanecarbaldehyde 
• 69036-26-6 (S)-1-cyclohexylbut-3-en-1-ol 
• 97563-45-6 1-cyclohexylprop-2-yn-1-ol 
• 133216-88-3 (R)-1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-ol 
• 128241-52-1 (R)-1-cyclohexylprop-2-yn-1-ol 
• 111843-46-0 methyl (2S,3R)-3-cyclohexyloxiranecarboxylate 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 111902-61-5 (2R,3R)-3-cyclohexyl-2,3-epoxypropan-1-ol 

Downstream Products

• 1196532-11-2 (S)-3-(tert-butyldimethylsilyloxy)-1-cyclohexylpropan-1-ol 
• 113309-50-5 (S)-3-cyclohexyl-1,3-diacetoxypropane 

Relevant academic research and scientific papers

Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes

The half-sandwich ruthenium complexes 1-3 activate terminal alkynes toward anti-Markovnikov hydration and reductive hydration under mild conditions. These reactions are believed to proceed via addition of water to metal vinylidene intermediates (4). The functionalization of propargylic alcohols by metal vinylidene pathways is challenging owing to decomposition of the starting material and catalytic intermediates. Here we show that catalyst 2 can be employed to convert propargylic alcohols to 1,3-diols in high yield and with retention of stereochemistry at the propargylic position. The method is also amenable to propargylic amine derivatives, thereby establishing a route to enantioenriched 1,3-amino alcohol products. We also report the development of formal anti-Markovnikov reductive amination and oxidative hydration reactions to access linear amines and carboxylic acids, respectively, from terminal alkynes. This chemistry expands the scope of products that can be prepared from terminal alkynes by practical and high-yielding metal-catalyzed methods.

Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation

Safe from protection! A pronounced kinetic preference for primary alcohol dehydrogenation enables the site-selective iridium catalyzed C-C coupling of polyols with allyl acetate in the absence of protecting groups, premetallated reagents, chiral auxiliaries, and discrete alcohol-to-aldehyde oxidation.

Symmetrie macrocycles by a prins dimerization and macrocyclization strategy

A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhen

Synthesis of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists: Application of the cis-thermal elimination of carbonates to alkaloid synthesis

Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3-dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyridine 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190°C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydropyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.

SmI2-INDUCED HIGHLY REGIOSELECTIVE REDUCTION OF α,β-EPOXY ESTERS AND γ,δ-EPOXY-α,β-UNSATURATED ESTERS. AN EFFICIENT ROUTE TO OPTICALLY ACTIVE β-HYDROXY AND δ-HYDROXY ESTERS

α,β-Epoxy esters were rapidly reduced at room temperature to yield β-hydroxy esters with retention of the configurations at the β-carbon atoms by using SmI2-THF-HMPA system in the presence of N,N-dimethylaminoethanol (DMAE).The conditions were successfully applied to the synthesis of vinylogous δ-hydroxy esters.