143463-40-5

Upstream product

• 19342-01-9 (S)-N,N-dimethyl-1-phenylethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 135190-26-0 2-[(R)-1-(dimethylamino)ethyl]benzenethiol 
• 74-88-4 methyl iodide 
• 91531-32-7 (R)-2-(1-Dimethylamino-ethyl)-thioanisol 

Downstream Products

• 147838-87-7 (-)-N,N-dimethyl-1-<2-(2-oxoheptylsulfinyl)phenyl>ethylamine 

Relevant academic research and scientific papers

Novel approach to the synthesis of enantioenriched sulfoxides. Highly diastereoselective alkylation of sulfenate anions with 1,4-asymmetric induction

(equation presented) Efficient 1,4-asymmetric induction with an enantiopure aminoalkyl group as the chiral auxiliary has been achieved in the first example of diastereoselective alkylation (up to 98:2) of a sulfenate anion, readily prepared by oxidation of the corresponding thiolate. The stereochemistry of the sulfoxide produced is the opposite of that obtained by the conventional route based on oxidation of the sulfide precursor.

Ortho-sulfenylation of N,N-dimethyl-1-phenylethylamine and oxidation of the resultant sulfides

The ortho-lithiation of chiral N,N-dimethyl-1-phenylethylamine (1) followed by sulfenylation and oxidation of the resulting sulfides afforded chiral sulfoxides 3 and 4. Use of sodium perborate as the oxidant gave the highest de.