1309831-76-2

Upstream product

• 132283-68-2 2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 1309831-72-8 (S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene 
• 1309831-74-0 (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide 

Downstream Products

• 1309831-77-3 (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4747-98-2 S-(-)-Norlaudanosine 
• 523-02-4 (S)-(-)-norcoralydine 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-(-)-xylopinine. Use of the sulfinyl group as an ipso director in aromatic SE

Optically pure (S)-(-)-xylopinine 2 was prepared in three steps in 52% overall yield. Thus, condensation of the carbanion derived from (S)-4 with the (S)-(E)-sulfinylimine 5 gave a 2:1 mixture of tetrahydroisoquinolines 6a and 6b, differing only in configuration at sulfur. N-Desulfinylation of this mixture gave the diastereomeric sulfoxides which, without separation, were converted into (S)-(-)-xylopinine (2) with loss of the sulfinyl moieties under Pictet-Spengler conditions. This unprecedented ipso electrophilic substitution of a sulfinyl group may have synthetic implications beyond that described in this work.