139750-85-9

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 139750-81-5 (R)-(+)-Ethynyl o-nitrophenyl sulfoxide 
• 139750-84-8 Trimethyl-((S)-2-nitro-benzenesulfinylethynyl)-silane 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 139750-82-6 (S_S)-(-)-Menthyl o-nitrobenzenesulfinate 

Downstream Products

• 139750-86-0 (1S,S_R)-6,7-dimethoxy-1-(o-nitrophenylsulfinylmethyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Chiral Acetylenic Sulfoxide in Enantioselective Synthesis of Tetrahydroisoquinoline and Tetrahydro-β-carboline Alkaloids. Total Synthesis of (R)-(+)-Carnegine and (R)-(+)-Tetrahydroharman

Michael addition of 2-(3,4-dimethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity.Optically pure (R)-(+)-carnegine and (R)-(+)-tetrahydroharman have been synthesized.

Chiral acetylenic sulfoxide in alkaloid synthesis. Total synthesis of (R)-(+)-carnegine

Remarkable diastereoselectivity was observed in the cyclization of β-aminovinyl sulfoxide 5a prepared from chiral acetylenic sulfoxide 1a in acidic medium. The cyclized product 6a was then converted to (R)-(+)-carnegine.