129016-19-9

Upstream product

• 927-77-5 n-propylmagnesium bromide 
• 144539-55-9 (+)-(S)-1-bromovinyl-p-tolyl sulfoxide 
• 144712-62-9 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-propanesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 63268-43-9 (+)-(S)-dimethyl-p-tolylsulfinylmethanephosphonate 
• 59336-80-0 1,2-Dibrom-1-p-tolylsulfinylethan 
• 54828-68-1 (R)-p-tolyl vinyl sulfoxide 
• 21865-09-8 p-tolyl propyl sulfoxide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 211424-31-6 (3R,4R)-3-Chloro-3-((R)-toluene-4-sulfinyl)-octan-4-ol 

Relevant academic research and scientific papers

A novel route to enantiomerically pure sulfoxides through displacement of a carbon leaving group

Enantiomerically pure sulfoxides were produced by reaction of dimethyl (S)-p-tolyl-sulfinylmethylphosphonate with the suitable Grignard reagents. Yields up to 75% were obtained.

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

Optically active sulfoxides by enantiospecific reactions of bromovinyl aryl sulfoxides with grignard reagents

Optically active bromovinyl aryl sulfoxides were subjected to reactions with phenyl- or alkyl-magnesium compounds, with the production of optically active diaryl or aryl alkyl sulfoxides, with inversion of configuration. The enantiospecificity of the process was found to be 98-100%.

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.