99930-84-4

Upstream product

• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 1066-54-2 trimethylsilylacetylene 
• 61210-52-4 (trimethylsilyl)ethynylmagnesium bromide 

Downstream Products

• 118090-00-9 (+)-(S)_S-p-tolylsulfinyl-2 trimethylsilyl-3<1R,4S>bicyclo<2.2.1>heptadiene-2,5 
• 118090-01-0 (-)-(S)_S-p-tolylsulfinyl-2 trimethylsilyl-3<1S,4R>bicyclo<2.2.1>heptadiene-2,5 
• 148731-51-5 [2-(1H-Indol-3-yl)-ethyl]-[(Z)-2-((R)-toluene-4-sulfinyl)-vinyl]-amine 
• 148731-49-1 [2-(3,4-Dimethoxy-phenyl)-ethyl]-[(Z)-2-((R)-toluene-4-sulfinyl)-vinyl]-amine 
• 124687-78-1 (1R,R_S)-3,4-dihydro-6,7-dimethoxy-1-<(p-tolylsulfinyl)-methyl>isoquinoline 
• 124687-77-0 (1S,R_S)-3,4-dihydro-6,7-dimethoxy-1-<(p-tolylsulfinyl)-methyl>isoquinoline 
• 99930-83-3 (R)-ethynyl-p-tolyl-sulfoxide 

Relevant academic research and scientific papers

Asymmetric approaches to cyclopentenones in the Ni(0)-promoted cyclocarbonylation reaction of allyl halides and acetylenes

Different approaches to the asymmetric synthesis of cyclopentenones by means of the Ni(CO)4-promoted alkyne-allyl halide cyclization-carbonylation are reported. The use of acetylenic sulfoxides 1 has proved effective for the synthesis of acyclic, fused [5+8], and spiro [5+5], [5+7], and [5+8] cyclopentenones, whereas placement of the aryl sulfoxide on the allylic system failed to afford any cycloadduct. Homochiral fused [5+8], and spiro [5+7] and [5+8] cyclopentenones have been obtained by this methodology. Finally, a modest enantioselectivity was observed when different homochiral α-substituted carboxylates were used as ligands in our reaction system.

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.