116386-53-9

Upstream product

• 118271-35-5 (R_S)-2-phenylethyl p-tolyl sulfoxide 
• 31350-92-2 (+)-(S_S)-chloromethyl (4-methylphenyl) sulfoxide 
• 3277-89-2 phenethylmagnesium bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 31350-91-1 (R)-chloromethyl p-tolyl sulfoxide 
• 100-39-0 benzyl bromide 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 1517-68-6 (S)-1-phenylpropan-2-ol 
• 935662-21-8 (S)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1142-21-8 (Z)-1,4-diphenylbut-2-ene 
• 1142-22-9 (E)-1,4-diphenylbut-2-ene 
• 622-24-2 2-phenylethyl chloride 
• 6378-07-0 ethyl (p-tolyl)sulfoxide 
• 30506-35-5 butyl(p-tolyl)sulfoxide 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 136121-38-5 (3R)-2-Chloro-1-phenyl-1-penten-3-ol 

Relevant academic research and scientific papers

A NOVEL APPROACH TO THE SYNTHESIS OF CHIRAL EPOXIDES AND ALLYLIC ALCOHOLS BY THE USE OF OPTICALLY ACTIVE p-TOLYL SULFINYL GROUP AS A CHIRAL AUXILILIARY

A Novel synthesis of chiral epoxides and allylic alcohols was realized from (-)-chloromethyl p-tolyl sulfoxide and carbonyl compounds through the α,β-epoxy sulfoxides.The procedure and a stereochemistry of the asymmetric induction of the reaction are repo

Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids

Putative enantioenriched carbenoid species, (R)-1-chloro-2- phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(Rs,R)-1- chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.

Highly enantiomerically enriched α-haloalkyl grignard reagents

α-Chloro- and α-bromoalkyl Grignard reagents 11 and 30 with > 97% ee (enantiomeric excess) were generated by a sulfoxide/magnesium exchange reaction from the enantiomerically and diastereomerically pure sulfoxides 25 and 27. The resulting α-haloalkyl Grig

A Novel Approach to the Asymmetric Synthesis of Epoxides, Allylic Alcohols, α-Amino Ketones, and α-Amino Aldehydes from Carbonyl Compounds through α,β-Epoxy Sulfoxides Using the Optically Active p-Tolylsulfinyl Group To Induce Chirality

A practical and relatively inexpensive procedure for the preparation of (-)-chloromethyl p-tolyl sulfoxide of high optical purity was accomplished by the chlorination of optically pure (+)-methyl p-tolyl sulfoxide with N-chlorosuccinimide in the presence of K2CO3.The (-)-chloromethyl p-tolyl sulfoxide was alkylated to give a diastereomeric mixture of (-)-1-chloroalkyl p-tolyl sulfoxides.Addition of the anion derived from these sulfoxides to ketones or aldehydes afforded chlorohydrins in quite good yields with complete 1,2-asymmetric induction.Treatment of these chlorohydrins with a base gave optically active α,β-epoxy sulfoxides.On treatment with n-BuLi, the α,β-epoxy sulfoxides gave epoxides or allylic alcohols of high optical purity.This novel procedure was applied to a short synthesis of optically active (+)-disparlure, the sex attractant of the female gypsy moth.Aminolysis of the α,β-epoxy sulfoxides gave optically active α-amino ketones and α-amino aldehydes in quite good yields.

THE PRACTICAL PROCEDURE FOR A PREPARATION OF 1-CHLOROALKYL p-TOLYL SULFOXIDES IN HIGH OPTICALLY ACTIVE FORM: A VERY SHORT SYNTHESIS OF OPTICALLY ACTIVE DISPARLURE

A chlorination of optically active alkyl p-tolyl sulfoxides with N-chlorosuccinimide in dichloromethane in the presence of potassium carbonate afforded optically active 1-chloroalkyl p-tolyl sulfoxides in 87-94percent ee (88-94percent chemical yields).The optically active chloroalkyl sulfoxide was applied to a synthesis of optically active (+)-disparlure.