477339-39-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-2-((1-HYDROXY-3,3-DIMETHYLBUTAN-2-YLIMINO)METHYL)-4,6-DIIODOPHENOL, 97% is used as a key intermediate for the synthesis of various pharmaceuticals, particularly those with chiral centers. Its unique structure allows for the development of enantiomerically pure drugs, which can exhibit different pharmacological properties and reduce potential side effects.
Used in Organic Synthesis:
In the field of organic chemistry, (S)-(-)-2-((1-HYDROXY-3,3-DIMETHYLBUTAN-2-YLIMINO)METHYL)-4,6-DIIODOPHENOL, 97% serves as a versatile building block for the synthesis of complex organic molecules. Its functional groups can be further modified to create a wide range of compounds with diverse applications.
Used in Catalytic Asymmetric Sulfoxidation:
(S)-(-)-2-((1-HYDROXY-3,3-DIMETHYLBUTAN-2-YLIMINO)METHYL)-4,6-DIIODOPHENOL, 97% is used as a catalyst in the asymmetric sulfoxidation of alkyl aryl sulfides. This process is crucial for the synthesis of enantiomerically pure sulfoxides, which are important intermediates in the pharmaceutical and agrochemical industries.
Used in Kinetic Resolution of Alkyl Aryl Sulfoxides:
(S)-(-)-2-((1-HYDROXY-3,3-DIMETHYLBUTAN-2-YLIMINO)METHYL)-4,6-DIIODOPHENOL, 97% is also utilized in the kinetic resolution of alkyl aryl sulfoxides, a process that allows for the separation of enantiomers and the production of optically pure compounds. This is particularly important in the development of single-enantiomer drugs, which can have improved efficacy and reduced side effects compared to their racemic counterparts.

InChI:InChI=1/C13H17I2NO2/c1-13(2,3)11(7-17)16-6-8-4-9(14)5-10(15)12(8)18/h4-6,11,17-18H,7H2,1-3H3/b16-6+/t11-/m1/s1

Upstream product

• 2631-77-8 3,5-diodosalicylaldehyde 
• 3907-02-6 (2R)-2-amino-3,3-dimethylbutan-1-ol 
• 112245-13-3 (S)-tert-leucinol 

Relevant academic research and scientific papers

On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing

We provide herein a mechanistic analysis of aryl sulfoxide excited state processes, inspired by our recent report of aryl sulfoxide based fluorescent chemosensors. The use of aryl sulfoxides as reporting elements in chemosensor development is a significan

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Copper-catalyzed asymmetric oxidation of sulfides

Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of th

Chiral sulfoxides as metabolites of 2-thioimidazole-based p38α mitogen-activated protein kinase inhibitors: Enantioselective synthesis and biological evaluation

Figure Presented. A number of pharmaceutically important drugs contain asymmetric sulfinyl moieties, so the biological evaluation of chiral sulfoxides as human drug metabolites is important for the development of safe and effective pharmaceuticals. Asymme

Enantioselective vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones using β-amino alcohol derived schiff base ligands

The asymmetric vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones by β-amino alcohol-derived Schiff base ligands with two stereogenic centers was investigated. Using aqueous hydrogen peroxide as the oxidant and the Schiff base 3b as

Synthesis, characterization, and structures of oxovanadium(v) complexes of Schiff bases of β-amino alcohols as tunable catalysts for the asymmetric oxidation of organic sulfides and asymmetric alkynylation of aldehydes

Oxovanadium(v) complexes 3a-3k and 4a-4d with general formula VO(L 3*)(OR5) were prepared in quantitative yields in alcohol (R5OH) from reactions of VO(O-i-Pr)3 and tridentate Schiff bases of β-amino alcohols having one or two stereogenic centers, (HO)C*(R1)(R2)C*H(R 3)NCH(2-OH-3,5-R42-C6H2) (H2L3*). The alkoxy OR5 ligand exchanges readily with the alcoholic molecule in the solvent. Crystal structures of 3b, 3f, 3i, and 4a were determined to be five-coordinate square pyramidal monomers. However, 1H NMR spectra of the complexes reveal two sets of signals, indicating the presence of two isomers in solution. The two isomers are suggested to be the endo/exo pair or the monomer/dimer pair. Asymmetric oxidations of methyl phenyl sulfide catalyzed by catalyst precursors 3 were demonstrated to afford the chiral sulfoxide in yields and ee values similar to those obtained from the in situ-formed catalytic systems of VO(acac)2 and corresponding Schiff base ligands. Complexes 3 and 4 are also good catalysts for asymmetric alkynyl additions to aldehydes. Structural differences between the oxovanadium complexes, for inducing high stereoselectivities in the asymmetric oxidation of organic sulfides and the asymmetric alkynyl addition to aldehydes, are rationalized. This journal is The Royal Society of Chemistry.

Investigations on the iron-catalyzed asymmetric sulfide oxidation

The development of an enantioselective sulfide oxidation involving a chiral iron catalyst and aqueous hydrogen peroxide as oxidant is described. In the presence of a simple carboxylic acid, or a carboxylate salt, the reaction affords sulfoxides with remarkable enantioselectivities (up to 96% ee) in moderate to good yields. The influence of the structure of the additive on the reaction outcome is reported. In the sulfoxide-to-sulfone oxidation a kinetic resolution (with s = 4.8) occurs, which, however, plays only a negligible role in the overall enantioselective process. Furthermore, a positive nonlinear relationship between the ee of the product and that of the catalyst has been found. On the basis of these observations, a possible catalyst structure is proposed.

Enantioselective sulfide oxidation with H2O2: A solid phase and array approach for the optimisation of chiral Schiff base-vanadium catalysts

Two libraries of chiral Schiff base ligands were synthesised and screened in the vanadium-catalysed oxidation of alkyl aryl sulfides with hydrogen peroxide as terminal oxidant. The vanadium-chiral Schiff base complex 10, readily prepared from 3,5-diiodo-salicylaldehyde and (S)-tert-leucinol, was found to be highly enantioselective. Optically active sulfoxides could thus be obtained in good yields with up to 97% ee.