301832-52-0

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 612035-98-0 O-but-2-en-1-yl N-tosylcarbamate 
• 183379-78-4 N-(1-hydroxybut-3-en-2-yl)-4-methylbenzenesulfonamide 
• 138212-37-0 3-p-toluenesulfonyl-4-vinyl-1,3-oxazolidin-2-one 
• 4083-64-1 Tosyl isocyanate 
• 1297141-69-5 (S)-1-((tert-butyldimethylsilyl)oxy)but-3-en-2-amine 
• 24458-20-6 methyl (2S)-4-(methylsulfanyl)-2-[[(4-methylphenyl)sulfonyl]amino]butanoate 
• 139696-34-7 (2S)-N-(4-toluenesulfonyl)-2-amino-4-methylsulfanyl-butanol 

Downstream Products

• 150674-62-7 (S)-N-[1-(methoxy)methoxy-3-buten-2-yl]-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

Palladium(II)-catalyzed oxidative cyclization of allylic tosylcarbamates: Scope, derivatization, and mechanistic aspects

A highly selective oxidative palladium(II)-catalyzed (Wacker-type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl-protected vinyl-oxazolidinones, common precursors to syn-1,2-amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans-amidopalladation of the olefin followed by β-hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck-, Wacker-, and metathesis reactions.

Radical cyclization in heterocycle synthesis. Part 10: A concise synthesis of (-)-kainic acid via sulfanyl radical addition-cyclization-elimination reaction

Sulfanyl radical addition-cyclization-elimination of diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidine in high yield. This reaction was extended to a radical cyclization using a catalytic amount of thiophenol. A successful application was demonstrated by the asymmetric synthesis of (-)-kainic acid. (C) 2000 Elsevier Science Ltd.