62258-06-4

Upstream product

• 1517-69-7 (R)-1-phenylethanol 
• 507-09-5 tiolacetic acid 
• 2449-49-2 dimethyl(1-phenylethyl)amine 
• 10387-40-3 potassium thioacetate 
• 3756-40-9 (S)-(-)-α-phenethyl bromide 

Downstream Products

• 1292296-55-9 (4-chlorophenyl)methylthiocarbamic acid S-((S)-1-phenylethyl) ester 
• 1292296-52-6 methyl-p-tolylthiocarbamic acid (S)-1-phenylethyl ester 
• 1292296-53-7 (4-methoxyphenyl)methylthiocarbamic acid S-((S)-1-phenylethyl) ester 
• 1292296-54-8 (2-methoxyphenyl)methylthiocarbamic acid S-((S)-1-phenylethyl) ester 
• 1292296-56-0 (3-chlorophenyl)methylthiocarbamic acid (S)-1-phenylethyl ester 
• 1292296-57-1 (4-cyanophenyl)methylthiocarbamic acid (S)-1-phenylethyl ester 
• 1292296-58-2 methyl(2,4,6-trimethylphenyl)thiocarbamic acid (S)-1-phenyl-ethyl ester 
• 1292296-59-3 methylnaphthalen-1-ylthiocarbamic acid (S)-1-phenylethyl ester 
• 1292296-60-6 C₁₆H₁₆FNOS 
• 1292296-69-5 methylthiocarbamic acid (S)-1-(3-chlorophenyl)-1-phenylethyl ester 
• 1292296-71-9 methylthiocarbamic acid (S)-1-naphthalen-1-yl-1-phenylethyl ester 
• 1292296-76-4 (S)-1-(4-methylphenyl)-1-phenylethanethiol 
• 1292296-77-5 (+/-)-1-(4-methoxyphenyl)-1-phenylethanethiol 
• 1292296-79-7 (S)-1-(4-chlorophenyl)-1-phenylethanethiol 

Relevant academic research and scientific papers

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

Copper-Catalyzed Stereospecific C-S Coupling Reaction of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Methyl Triflate

A one-pot protocol for the synthesis of highly enantiopure benzylic thioethers, thioacetates, and sulfones (94-99% ee) via a ligand-free, copper-catalyzed stereospecific C-S coupling reaction of thiols and enantioenriched tertiary benzylic amines via in situ activation by methyl triflate is developed. Various enantioenriched tertiary benzylic amines, including 1-arylalkylamines, 1-tetrahydronaphthylethylamine, heterocyclic amines (e.g., 1-(thiophen-2-yl)ethanamine), and amino acid esters containing a benzylamine moiety, are highly efficient substrates, and their chirality is efficiently transferred to the products (94-99% ee). The absolute configurations of the products are predictable and follow the pattern of SN2-type substitutions; an inversion of the absolute configuration of the tertiary amines occurs during the C-S coupling reaction. Not only are various alkene-, arene-, and heteroarenethiols suitable for this C-S coupling reaction but also potassium thioacetate and sodium phenylsulfinate are as well. A plausible mechanism was proposed on the basis of the experimental results.

Ligand dependence of the synthetic approach and chiroptical properties of a magic cluster protected with a bicyclic chiral thiolate

Chiral gold clusters stabilised by enantiopure thiolates were prepared, size-selected and characterised by circular dichroism and mass spectrometry. The product distribution is found to be ligand dependent. Au25 clusters protected with camphorthiol show clear resemblance of their chiroptical properties with their glutathionate analogue. The Royal Society of Chemistry 2012.

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Lithiation of N-aryl S-α-alkylbenzyl thiocarbamates leads to rearrangement with migration of the N-aryl ring to the anionic centre α to S, a process which generally proceeds with ca. 98% retention of stereochemistry and returns chiral benzylic tertiary thiols in high enantiomeric ratios.

A convenient method for the preparation of alkyl aryl sulfides from alcohols and (chloromethylene)dimethylammonium chloride

(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent), prepared easily from DMF and oxalyl chloride, works as an efficient condensation reagent for the thioetherification of alcohols in one-pot under mild conditions. Various alcohols are successively converted into the corresponding sulfides with inversion of configurations in moderate to high yields. Copyright

The configurational stability of an enantioenriched α-thiobenzyllithium derivative and the stereochemical course of its electrophilic substitution reactions; synthesis of enantiomerically pure, tertiary benzylic thiols

The lithium compound (S)-7, formed by deprotonation of the (S)-S-1-phenylethyl thiocarbamate (S)-10, is configurationally stable at -70°C. Even at elevated temperatures it racemizes only very slowly. It represents the first essentially enantiopure αthioca

A Highly Enantiomerically Enriched α-Thiobenzyl Derivative with Unusual Configurational Stability

Keywords: carbanions; chirality; configuration inversion; ion pairs; lithium

ENANTIOSELECTIVE ROUTES TO CHIRAL BENZYLIC THIOLS, SULFINIC ESTERS AND SULFONIC ACIDS ILLUSTRATED BY THE 1-PHENYLETHYL SERIES

Chiral benzylic thiols, sulfinic esters and sulfonic acids can be produced readily and in excellent enantiomeric purity from the corresponding achiral ketones.