1353374-01-2

Upstream product

• 22557-04-6 1-(but-3-yn-1-yl)-4-methylbenzene 
• 1332955-36-8 6-(p-tolyl)hex-3-yn-1-ol 
• 1332954-74-1 (Z)-6-(p-tolyl)hex-3-en-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1332955-46-0 C₁₃H₁₉N 
• 1332954-96-7 (Z)-4-methyl-N-(6-p-tolylhex-3-enyl)benzenesulfonamide 
• 1332955-18-6 (Z)-6-(p-tolyl)hex-3-ene-1-thiol 
• 1332955-52-8 C₁₅H₂₀OS 
• 1332955-42-6 C₁₃H₁₇N₃ 

Relevant academic research and scientific papers

Tandem Prins/friedel-crafts cyclization for stereoselective synthesis of heterotricyclic systems

Homoallylic substrates such as (E)-6-arylhex-3-enyl alcohols, N-tosylamides, and thiols undergo smooth cross-coupling with various aldehydes in the presence of 10 mol % Sc(OTf)3 and 30 mol % TsOH to afford the trans-fused hexahydro-1H-benzo [f]isochromenes, N-tosyloctahydrobenzo [f] -isoquinolines, and hexahydro-lH-benzo [f]isothiochromenes, respectively. However, the cross-coupling of (Z)-olefins such as 6-arylhex-3-enyl alcohols, N-tosylamides, and thiols with aldehydes affords the corresponding hexahydro-1H-benzo-[f]isochromenes, N-tosyloctahydrobenzo [f]isoquinolines, and hexahydro-1H-benzo[f] isothiochromenes with complete cis selectivity via intramolecular Prins-, aza-Prins-, and thia-Prins/(Figure presented) Friedel - Crafts cyclizations, respectively. Though the Prins cyclization proceeds smoothly under the influence of Sc(OTf)3, high conversions and enhanced reaction rates are achieved using a mixture of Sc(OTf)3 and TsOH (1:3).