343239-88-3

Upstream product

• 20187-61-5 mesyloxyacetophenone 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 20780-53-4 (R)-Styrene oxide 
• 685835-75-0 (1R)-2-O-methanesulfonyl-1-phenyl-1-O-vinyl-1,2-ethanediol 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 

Relevant academic research and scientific papers

Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts

A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).

METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE 2-SULFONYLOXY-1-PHENYLETHANOL DERIVATIVES

Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an α-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.

Synthesis, biological, and chiroptical activity of 3-phenyl-clavams

The [2+2]cycloaddition of chlorosulfonyl isocyanate to simple vinyl ethers derived from the 2-O-sulfonylated (R) and (S) 1-phenyl-1,2-ethanediol leads to 4-alkoxy-azetidin-2-ones with a moderate stereoselectivity. The cycloaddition to analogous (Z)-propenyl ethers proceeds stereospecifically with the retention of the olefin configuration. The intramolecular alkylation of β-lactam nitrogen atom furnished all possible stereoisomers of 3-phenyl- and 6-methyl-3-phenyl-clavams. The biological and chiroptical activity of synthesized clavams was investigated. The (3R,5R)-diastereomer 30 showed higher inhibition of bacterial enzymes than other related compounds.

Process for the preparation of enantiomerically pure 3-phenyl-3-hydroxypropylamine

The present invention relates to an improved process for the synthesis of enantiomerically pure 3-phenyl-3-hydroxypropylamine of formula I; more particularly the present invention relates to the said process using styrene; the synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the target compound, using styrene, a readily accessible starting material gives the optically pure dihydroxy compound (ee >97%; the selective monotosylation of primary alcohol, nucleophilic displacement by cyano and subsequent reduction to amino group furnishes the desired 3-phenyl-3-hydroxypropylamine in enatiomerically pure form, a key intermediate in the synthesis of variety of oxetine related anti-depressant drugs.

Acetalsulfonate derivative, process for producing the same, and process for producing styrene oxide derivative

There are provided an acetalsulfonate derivative useful as an intermediate for medicines and agricultural chemicals, a process for industrially producing the derivative, and a process for industrially producing a styrene oxide derivative from the acetalsulfonate derivative or from a mandelic acid derivative. A process for producing an acetalsulfonate derivative which comprises a first step of esterifying a mandelic acid derivative to form a mandelic ester derivative, a second step of protecting the mandelic ester derivative by an acetal to form an acetal derivative, a third step of reducing the acetal derivative to form an ethanediol derivative and a fourth step of reacting the ethanediol derivative with a sulfonyl chloride derivative. A process for producing a styrene oxide derivative which comprises a deprotecting step of deacetalizing the acetalsulfonate derivative and a step of epoxidizing the sulfonate derivative obtained in the deprotecting step with the aid of a base catalyst.