1226896-38-3

Usage

Uses

Used in Organic Synthesis:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is utilized as a chiral building block for the synthesis of various organic compounds. Its specific stereochemistry contributes to the creation of enantiomerically pure products, which is crucial for the development of pharmaceuticals and agrochemicals with desired biological activities.
Used in Catalyst and Ligand Design:
In the field of catalysis, (R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene serves as a precursor for the design and synthesis of chiral catalysts and ligands. Its reactivity and structural features enable the development of catalysts that can selectively promote specific reactions, enhancing the efficiency and selectivity of chemical processes.
Used in Research and Development:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is also employed in academic and industrial research settings. Its unique properties make it an important tool for investigating the mechanisms of asymmetric reactions and for the discovery of new chiral compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is used as a key intermediate in the synthesis of chiral drugs. Its ability to produce enantiomerically pure compounds is essential for the development of drugs with improved efficacy and reduced side effects, as the biological activity of enantiomers can differ significantly.
Used in Agrochemical Industry:
In the agrochemical sector, (R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is utilized as a starting material for the synthesis of chiral pesticides and herbicides. The production of enantiomerically pure compounds ensures that only the desired enantiomer with the required biological activity is used, reducing the environmental impact and improving the safety of these chemicals.
Used in Materials Science:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is also applied in the development of chiral materials with specific properties, such as optical activity or selectivity in molecular recognition. These materials have potential applications in various fields, including sensors, catalysts, and advanced materials for electronics and photonics.

Upstream product

• 1226896-33-8 (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid 
• 1255651-84-3 dimethyl-2,2'-((2-(diacetoxy-λ³-iodanyl)-1,3-phenylene)bis(oxy))(2R,2'R)-dipropionate 
• 88-05-1 2,4,6-trimethylaniline 
• 1255651-99-0 (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate 
• 41046-67-7 2-iodoresorcinol 
• 108-46-3 recorcinol 

Downstream Products

• 1226896-63-4 (2,6-bis(((R)-1-(mesitylamino)-1-oxopropan-2-yl)oxy)-phenyl)-λ³-iodanediyl diacetate 

Relevant academic research and scientific papers

Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators

The enantioselective electrochemical lactonization of diketo acid derivatives using chiral iodoarenes as redox mediators is reported for the first time. Good to high stereoselectivities are observed in the lactonization and also in intermolecular α-alkoxylations of diketo ester derivatives. This enantioselective process was then adapted to an electrochemical flow microreactor where only small amounts of supporting electrolyte were necessary.

Hypervalent Iodine(III)-Catalysed Enantioselective α-Acetoxylation of Ketones

An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 percent with enantioselectivities up to 88 percent ee are obtained using only low catalyst loadings of only 5 mol percent under mild reaction conditions.

Synthesis of Polycyclic Cyclohexadienone through Alkoxy-Oxylactonization and Dearomatization of 3′-Hydroxy-[1,1′-biphenyl]-2-carboxylic Acids Promoted by Hypervalent Iodine

Alkox-oxylactonization and dearomatization of 3′-hydroxy-[1,1′-biphenyl]-2-carboxylic acid simultaneously promoted by hypervalent iodine have been developed using stoichiometric PhI(OAc)2 or a catalytic amount of chiral aryl-λ3-iodane generated in situ. This reaction provides a concise method to synthesize diverse polycyclic cyclohexadienones as potential inhibitors of DNA polymerase under mild reaction conditions.

Chiral hypervalent iodine(III) catalyst promotes highly enantioselective sulfonyl-and phosphoryl-oxylactonizations

An efficient enantioselective hypervalent iodine promoted oxylactonization of 4-pentenoic acids has been achieved using stoichiometric or a catalytic amount of chiral aryl-λ3-iodane. This reaction provides straightforward access to a wide range of sulfonyloxy-and phosphoryloxy-γ-butyrolactones in respectable yields with moderate to excellent enantioselectivities.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.

Chiral Aryliodine-Mediated Enantioselective Organocatalytic Spirocyclization: Synthesis of Spirofurooxindoles via Cascade Oxidative C-O and C-C Bond Formation

An enantioselective organocatalytic oxidative spirocyclization of alkyl 3-oxopentanedioate monoamide derivatives leading to the formation of diverse spirofurooxindoles with high enantioselectivity has been realized via chiral aryliodine-mediated cascade C-O and C-C bond formations. The reaction is postulated to proceed via oxidative C-O bond formation followed by oxidative C-C bond formation, with the latter being the enantioselectivity-determining step.

Enantioselective kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine (iii) species

"Chemical Equation Presented" The iodines(lll) have it: The rational design of a conformationals/ flexible C2symmetric iodosylarene catalyst has been used for the enantioselective Kita oxidative spirolactonization. The reaction occurs through secondary n-σ* or hydrogen-bonding interactions between the chiral catalyst and the substrate. Mes = mesityl (2,4,6-trimethylphenyl).

Chiral hypervalent iodine-catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones

We demonstrate here the rational design of a conformationally flexible C2-symmetric iodosylarene 8g based on secondary n-σ or hydrogen-bonding interactions as a chiral catalyst for the enantioselective Kita oxidative spirolactonization of 1-nap