120886-82-0

Upstream product

• 3406-03-9 2-(phenylsulfonyl)acetophenone 
• 121053-49-4 (R)-(+)-1-phenyl-2-(phenylthio)ethan-1-ol 
• 56751-12-3 2-chloro-1-phenylethanol 
• 23128-59-8 ω-bromo-ω-phenylsulfonylacetophenone 
• 5418-11-1 phenyl styryl sulfone 
• 873-55-2 sodium benzenesulfonate 
• 536-74-3 phenylacetylene 
• 109183-66-6 (R)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethyl p-toluenesulfonate 
• 33973-12-5 (S)-(+)-methyl 2-phenyl-2-(tetrahydropyranyloxy)acetate 
• 60168-63-0 (R)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 
• 21210-43-5 (S)-Methyl mandelate 
• 17199-29-0 (S)-Mandelic acid 
• 108-98-5 thiophenol 
• 20780-53-4 (R)-Styrene oxide 

Downstream Products

• 950478-21-4 (R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate 
• 105769-46-8 (R)-(+)-2-chloro-2-phenylethyl phenyl sulfone 

Relevant academic research and scientific papers

Synthesis of a biferrocene diphosphine ligand with only planar chirality and its application in the Rh-catalyzed asymmetric hydrogenation of β-keto sulfones

A new type of biferrocene diphosphine ligand bearing only planar chirality was developed and used in Rh(I)-catalyzed asymmetric hydrogenation of β-keto sulfones, giving the corresponding optically active β-hydroxy sulfones in excellent yields and in 72.4-

Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones

A series of optically active β-hydroxy sulfones has been obtained through an oxosulfonylation-stereoselective reduction sequence in aqueous medium. Firstly, β-keto sulfones were synthesized from arylacetylenes and sodium sulfinates to subsequently develop the carbonyl reduction in a highly selective fashion using alcohol dehydrogenases as biocatalysts. Optimization of the chemical oxosulfonylation reaction was investigated, finding inexpensive iron(III) chloride hexahydrate (FeCl3 ? 6H2O) as the catalyst of choice. The selection of isopropanol in the alcohol-water media resulted in high compatibility with the enzymatic process for enzyme cofactor recycling purposes, providing a straightforward access to both (R)- and (S)-β-hydroxy sulfones. The practical usefulness of this transformation was illustrated by describing the synthesis of a chiral intermediate of Apremilast. Interestingly, the development of a chemoenzymatic cascade approach avoided the isolation of β-keto sulfone intermediates, which allowed the preparation of chiral β-hydroxy sulfones in high conversion values (83–94 %) and excellent optical purities (94 to >99 % ee).

One-pot synthesis of chiral β-hydroxysulfones from alkynes: Via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O

A highly enantioselective synthesis of β-hydroxysulfones from inexpensive and readily available terminal alkynes and sodium sulfinates via a consecutive one-pot reaction in an aqueous medium under mild conditions is described. The intermediates, β-keto sulfones, generated from an aerobic oxysulfonylation of terminal alkynes and sodium sulfinates catalyzed by an iron salt in MeOH/H2O (v : v = 3 : 1) at 50 °C, were subsequently reduced by a Ru-catalyzed asymmetric transfer hydrogenation with HCOONa as a hydrogen source. A variety of chiral β-hydroxysulfones were obtained in good yields and up to 99.9% ee values. This one-pot process could be easily scaled up for gram-scale synthesis.

Chiral beta-hydroxyl sulfone and preparation method thereof

The invention relates to chiral beta-hydroxyl sulfone (formula I) and a preparation method thereof. The preparation method is a one-pot unsymmetrical cascade reaction, and comprises the following steps: (1) performing an oxygen-sulfonation reaction by usi

Highly enantioselective one-pot synthesis of chiral β-hydroxy sulfones via asymmetric transfer hydrogenation in an aqueous medium

A mild transformation in an aqueous medium for the one-pot synthesis of optically active β-hydroxy sulfones is described. The intermediates of β-keto sulfones obtained via a nucleophilic substitution reaction of α-bromoketones and sodium sulfinates in Hs

Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones

The α,β-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate β-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B2(pin)2] catalyzed by nonracemic CuI-diphosphine complexes to provide, upon subsequent oxidation, β-hydroxy sulfones in good yields and high enantiocontrol.

Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO2

A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized sidechains at the Lewis acidic boron atom in TarB-NO2 or the added steric bulk of the α-sidechain. As an alternative method, these substrates were synthesized using TarB-NO2 via a two-step procedure involving the reduction of an α-halo ketone to a chiral terminal epoxide, followed by regioselective/regiospecific epoxide opening by various nucleophiles. This procedure provides access to a variety of functionalized secondary alcohols including β-hydroxy ethers, thioethers, nitriles, and amines with enantiomeric excesses of 94% and yields up to 98%.

Dynamic kinetic resolution of β-keto sulfones via asymmetric transfer hydrogenation

The dynamic kinetic resolution of β-keto sulfones was achieved via asymmetric transfer hydrogenation using (S,S)-RuCl[N-(tosyl)-1,2- diphenylethylenediamine](p-cymene) in the presence of formic acid and triethylamine afforded the desired products in good

Optically active nitrile oxides: synthesis and 1,3-dipolar cycloaddition reactions

Baker's yeast-promoted reduction of the C{double bond, long}C bond in 2-aryl-1-nitropropenes gave the corresponding optically active (R)-2-aryl-1-nitropropanes of high enantiomeric purity (ee >90%). They were next converted with the aid of the Mukaiyama and Hoshino method into the optically active nitrile oxides, which were made to react in situ with ethyl propiolate, methylvinyl ketone and (R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate to yield the appropriate, enantiomerically enriched, isoxazoles or 4,5-dihydroisoxazoles as diastereomeric mixtures, respectively.

Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata

β-Keto sulfones bearing bulky groups are reduced with high enantioselectivities to the corresponding optically active β-hydroxy sulfones by the fungus Curvularia lunata CECT 2130; the cells can be re-used without loss of their catalytic activity.