118271-35-5

Upstream product

• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 103-63-9 1-phenyl-2-bromoethane 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 3277-89-2 phenethylmagnesium bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 879224-88-1 (+)-(S_S,S)-1-chloro-2-phenylethyl p-tolyl sulfoxide 
• 19134-46-4 1-phenyl-3-piperidino-2-butanone 
• 121174-12-7 (+)-(2S,3S)-2,3-epoxy-3-methyl-1-phenyl-4-(tert-butyldimethylsiloxy)butane 
• 117326-74-6 (-)-(2R,3S)-2,3-epoxy-2-methyl-4-phenylbutan-1-ol 
• 117326-76-8 (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol 
• 117326-75-7 (E)-(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol 
• 117326-77-9 [(2S,3R)-3-Benzyl-3-(tert-butyl-dimethyl-silanyl)-2-methyl-oxiranyl]-methanol 
• 121174-17-2 (R)-4-Hydroxy-3-methyl-1-phenyl-3-piperidin-1-yl-butan-2-one 
• 121174-18-3 (S)-4-Hydroxy-3-methyl-1-phenyl-3-piperidin-1-yl-butan-2-one 
• 121249-32-9 (2R,3S)-2-Benzyl-3-methyl-2-((R)-toluene-4-sulfinyl)-oxirane 
• 121174-16-1 (2R,3R)-2-Benzyl-3-methyl-2-((R)-toluene-4-sulfinyl)-oxirane 
• 121174-11-6 (R)-3-Chloro-2-methyl-4-phenyl-3-((R)-toluene-4-sulfinyl)-butan-2-ol 
• 117406-97-0 (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane 
• 117326-73-5 (-)-(2R,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane 

Relevant academic research and scientific papers

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.

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.