108268-29-7

Usage

Uses

Used in Pharmaceutical Industry:
(R,R)-(-)-1,2-CYCLOOCTANEDIOL is used as a chiral building block for the synthesis of various pharmaceuticals, leveraging its unique stereochemistry to produce enantiomerically pure compounds. This is crucial in the development of drugs with targeted therapeutic effects and reduced side effects, as the stereochemistry of a molecule can significantly influence its biological activity.
Used in Organic Synthesis:
In the field of organic synthesis, (R,R)-(-)-1,2-CYCLOOCTANEDIOL is employed as a key intermediate for the production of high-value chemicals. Its chiral nature allows for the creation of complex molecular structures with specific stereochemistry, which is essential for the development of new materials and compounds with tailored properties.
Used in Asymmetric Catalysis:
(R,R)-(-)-1,2-CYCLOOCTANEDIOL serves as a chiral ligand in asymmetric catalysis, a process that enables the selective formation of one enantiomer over another. This is vital for the synthesis of enantiomerically pure compounds, which are often required in various applications, including pharmaceuticals, agrochemicals, and fragrances.
Used in Resolving Racemic Mixtures:
As a resolving agent, (R,R)-(-)-1,2-CYCLOOCTANEDIOL is instrumental in the separation of racemic mixtures into their individual enantiomers. This process is essential for obtaining pure enantiomers, which can exhibit different biological activities and properties, making it a valuable tool in the purification and characterization of chiral compounds.

Upstream product

• 286-62-4 Cyclooctene oxide 
• 51075-28-6 2-bromo-3-phenylpropanal 
• 42565-22-0 trans-1,2-cyclooctanediol 
• 97-72-3 2-Methylpropionic anhydride 
• 931-87-3 (R)-(-)-(E)-cyclooctene 
• 931-89-5 (E)-cyclooctene 
• 69926-50-7 (1S,2S)-(Z)-cyclooct-5-ene-1,2-diol 
• 108-24-7 acetic anhydride 
• 78823-36-6 p-nitrobenzoic-propionic anhydride 
• 64-19-7 acetic acid 
• 117468-07-2 rel-(1S,2S,5Z)-cyclooct-5-en-1,2-diol 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 

Downstream Products

• 638-54-0 1,8-octanedial 
• 23299-33-4 10-Phenyl-9,11-trans-dioxabicyclo<6.3.0>undecan 

Relevant academic research and scientific papers

Synthesis of optically active bicyclo[3.3.0]octane Skeleton using transannular reaction

Optically active 5-cyclooctene-1,2-diol derivatives prepared by an enzymatic procedure have been converted into bicyclo[3.3.0]octane derivatives by transannular reaction with complete inversion of the stereogenic center linked to the leaving group. Formal synthesis of (+)-iridomyrmecin has been achieved starting from (S,S)-5-cyclooctene-1,2-diol by using this process.

Photochirogenic nanosponges: phase-controlled enantiodifferentiating photoisomerization of (Z)-cyclooctene sensitized by pyromellitate-crosslinked linear maltodextrin

Linear maltodextrin (LM) was cross-linked by pyromellitic dianhydride to afford LM polymers of different cross-linking degrees. When soaked in water, these cross-linked LM polymers (nanosponges (NSs)), evolved into several phases from sol to suspension, then to flowing gel, and finally to rigid gel with an increase in their content. Enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to chiral (E)-isomer (1E), which was employed as a benchmark reaction to quantitatively assess the environmental-to-molecular chirality transfer process, was performed in aqueous media containing these pyromellitate-crosslinked LM-NSs in different phases. The enantiomeric excess (ee) of 1E obtained was relatively insensitive to the phases at least up to the flowing gel phase, but became highly sensitive in the rigid gel phase, exhibiting an abrupt drop in the early rigid gel phase followed by a rapid recovery in the late rigid gel phase. A comparison with the phase-dependent ee profiles previously reported for similar pyromellitate-crosslinked cyclodextrin (CD)- and cyclic nigerosylnigerose (CNN)-NSs revealed that the chiral void space created around the pyromellitate linker in NS is responsible for the dramatic changes in ee in the rigid gel phase, whereas the inherent host cavity in CD/CNN plays only limited roles in the supramolecular photochirogenesis mediated by the sensitizer-crosslinked NSs. The latter insight allows us to further expand the applicable range of the present concept and methodology by employing a much wider variety of oligosaccharides as well as substrates and sensitizing cross-linkers.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification

We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.

En route to multicatalysis: Kinetic resolution of trans-cycloalkane-1,2- diols via oxidative esterification

We demonstrate the application of a multicatalyst to the oxidation of a broad variety of aldehydes and subsequent enantioselective esterification of the incipient acids with (±)-trans-cycloalkane-1,2-diols. This reaction operates well with a multicatalyst bearing two independent catalytic moieties that provide monoprotected 1,2-diols in one pot.

Enhanced rate and selectivity by carboxylate salt as a basic cocatalyst in chiral N-heterocyclic carbene-catalyzed asymmetric acylation of secondary alcohols

The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.

Enantioselective biooxidation of racemic trans-cyclic vicinal diols: One-pot synthesis of both enantiopure (S,S)-cyclic vicinal diols and (R)-α-hydroxy ketones

Highly regio- and enantioselective alcohol dehydrogenases BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis BGSC1A1), CDDHPm (cyclic diol dehydrogenase from Pseudomonas medocina TA5), and CDDHRh (cyclic diol dehydrogenase from Rhodococcus sp. Moj-3449) were discovered for the oxidation of racemic trans-cyclic vicinal diols. Recombinant Escherichia coli expressing BDHA was engineered as an efficient whole-cell biocatalyst for the oxidation of (±)-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,2-cycloheptane-diol, and 1,2-cyclooctanediol, respectively, to give the corresponding (R)-α-hydroxy ketones in >99% ee and (S,S)-cyclic diols in >99% ee at 50% conversion in one pot. Escherichia coli (BDHA-LDH) co-expressing lactate dehydrogenase (LDH) for intracellular regeneration of NAD+ catalyzed the regio- and enantioselective oxidation of (±)-1,2-dihydroxy-1,2,3,4- tetrahydronaphthalene to produce the corresponding (R)-α-hydroxy ketone in >99% ee and (S,S)-cyclic diol in 96% ee at 49% conversion. Preparative biotransformations were also demonstrated. Thus, a novel and useful method for the one-pot synthesis of both vicinal diols and α-hydroxy ketones in high ee was developed via high Copyright

Enantiomerically enriched trans-diols from alkenes in one pot: A multicatalyst approach

Multicatalysts consisting of non-natural oligopeptides with distinctly different catalytic moieties create molecular complexity in a multistep one-pot sequence starting from simple alkenes yielding highly enantiomerically enriched trans-diols. The Royal Society of Chemistry 2012.

Kinetic resolution of trans-cycloalkane-1,2-diols via Steglich esterification

We describe the efficient and highly enantioselective kinetic resolution of trans-cycloalkane-1,2-diols utilizing an enantioselective Steglich reaction with a variety of carboxylic acids that form the corresponding anhydrides in situ.

Enantioselective kinetic resolution of trans-cycloalkane-1,2-diols

Finally! The title resolution is achieved with a nonnatural, partially rigid, lipophilic tetrapeptide at low catalyst loadings without additional base or cosolvents. The transition-state model (ball-and-stick model in the scheme; C gray, N blue, O red) emphasizes the interplay between hydrogen-bonding and hydrophobic interactions. (Chemical Equation Presented)