392662-71-4

Upstream product

• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 392662-77-0 (R)-1-Benzyl-6,7-dimethoxy-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 392662-72-5 (R)-6,7-Dimethoxy-1-methyl-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 392662-73-6 (R)-6,7-Dimethoxy-1-propyl-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 392662-74-7 (R)-6,7-Dimethoxy-1-pentyl-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 392662-76-9 (R)-1-Isopropyl-6,7-dimethoxy-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 392662-75-8 (R)-1-Isobutyl-6,7-dimethoxy-2-((R)-toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinoline 
• 1426672-73-2 C₂₁H₂₆ClNO₃S 
• 47145-36-8 (1S)-1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Enantiopure tetrahydroisoquinolines via N-sulfinyl Pictet-Spengler reactions

Asymmetric Pictet-Spengler reactions with (R)-N-p-tolylsulfinyl-3,4-dimethoxyphenylethyl amine proceeded with high diastereoselectivity. Starting from the commercially available (R)- and (S)-Andersen reagents a highly efficient route to (+)- and (-)-salsolidine and related tetrahydroisoquinolines was developed.

Short stereoselective synthesis of (+)-crispine A via an N-sulfinyl Pictet-Spengler reaction

We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield.