54234-80-9

Upstream product

• 144712-61-8 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-propanesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 927-77-5 n-propylmagnesium bromide 
• 21865-09-8 p-tolyl propyl sulfoxide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 80684-96-4 (2R)-2-[(R)-p-tolylsulfinyl]butane 
• 258356-58-0 (2S)-2-[(R)-p-tolylsulfinyl]butane 

Relevant academic research and scientific papers

Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases

We report on the development of high-throughput fluorogenic assay that can streamline directed evolution of enantioselective sulfoxide reductases. As a model, methionine sulfoxide reductase A (MsrA) has been evolved to expand its limited substrate scope. The resulting mutant MsrA can resolve a range of new challenging racemic sulfoxides with high efficiency including the pharmaceutically relevant albendazole sulfoxide. The simplicity and the level of throughput make this method also suitable for the screening of metagenomic libraries in future for the discovery of new enzymes with similar reactivities.

Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach

A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.

Iron-catalyzed imidative kinetic resolution of racemic sulfoxides

Kinetic resolution of racemic sulfoxides requires either custom substrates or shows moderate enantioselectivity, leading to achiral coproducts (such as sulfones) as an intrinsic part of the process. A new strategy is demonstrated that allows the resolution of racemic sulfoxides through catalytic asymmetric nitrene-transfer reactions. This approach gives rise to both optically active sulfoxides and highly enantioenriched sulfoximines. By using a chiral iron catalyst and a readily available iodinane reagent, high selectivity factors have been achieved under very practical reaction conditions. With respect to the substrate scope, it is noteworthy that this unprecedented imidative kinetic resolution of racemic sulfoxides provides access to both aryl-alkyl and dialkyl sulfoximines in highly enantioenriched forms. Copyright

Stereoselective Reaction of α-Sulfinyl Carbanion Derived from Chiral 2-(Trialkylsilyl)ethyl Sulfoxides: Evidence for a Novel Silicon - Oxygen Interaction

Reactions of α-sulfinyl carbanions, derived from p-tolyl sulfoxides bearing various alkyl groups, with various electrophiles were examined. The reaction of α-sulfinyl carbanions, derived from the β-silylethyl sulfoxides, with ketones or trimethyl phosphate, gave the syn products with high stereoselectivity. Interaction between the silicon in the trialkylsilyl group and the carbonyl oxygen in nucleophiles was postulated to stabilize the transition state, leading preferably to the syn diastereisomers. This novel silicon-oxygen interaction was supported by an MO calculation study using the MOPAC 93/PM3 and the Gaussian 94 Beche3LYP/3-21+G* methods.

Asymmetric Synthesis of Alkane- and Arenesulfinates of Diacetone-D-glucose (DAG): An Improved and General Route to Both Enantiomerically Pure Sulfoxides

Diacetone-D-glucose (DAG), a commercially available, sugar-derived secondary alcohol, was found to react with alkane- and arenesulfinyl chlorides in the presence of a tertiary amine in a very useful manner.When i-Pr2NEt is used as the base, (-)-(S)-alkane- and arenesulfinates are obtained in 50-90percent yield with 89 - >/= 95percent de.Simply changing the base from i-Pr2NEt to Py affords (+)-(R)-alkane- or arenesulfinates in 56-87percent yield with 70 - >/= 95percent de.The de's were determined by (1)H NMR.Optically pure alkane- and arenesulfinates are obtained either by recrystallization or by column chromatography.These sulfinates were transformed into various enantiomerically pure sulfoxides (alkyl alkyl or alkyl aryl) by reaction with different Grignard reagents.This new methodology is cheap, quick, and very convenient when both enantiomers of a given sulfoxide are needed enantiomerically pure.The influence of the solvent, as well as the effect of other types of bases, on the stereochemical course of the reaction has been evaluated, and a possible origin of the diastereoselectivity is discussed.Other optically pure secondary alcohols are used in the same reaction, and the comparison of their behavior with that of DAG is also reported.