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• 14633-54-6 cyclopropylphenylsulfide 

Relevant academic research and scientific papers

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Chiral: N, N ′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide

A highly enantioselective sulfoxidation of various sulfides has been achieved by a N,N′-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

Peroxygenase-Catalyzed Enantioselective Sulfoxidations

The performances of the unspecific peroxigenase from Agrocybe aegerita (AaeUPO) in the asymmetric sulfoxidation of substituted aryl alkyl sulfides were here investigated. A small library of differently substituted aryl alkyl sulfoxides was successfully synthesized from the corresponding sulfides in the presence of AaeUPO and H2O2. All the sulfoxides were obtained as (R)-enantiomers, regardless the substitution pattern both on the aromatic ring and the alkyl chain, in up to > 99 % conversion and > 99 % ee. An overview about the biocatalytic entries to chiral sulfoxides is also presented here in form of a comparison between the results obtained with AaeUPO and performances of the chloroperoxidase from Caldariomyces fumago, and three different Baeyer–Villiger monooxygenases. To the best our knowledge, this is the first example of a systematic investigation of the AaeUPO synthetic potential in the asymmetric oxidation of hetero atoms, i.e., the pro-stereogenic sulfur of sulfides.

Asymmetric oxidation catalysis by a porphyrin-inspired manganese complex: Highly enantioselective sulfoxidation with a wide substrate scope

The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5-1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).