95069-01-5Relevant academic research and scientific papers
HIGH-PRESSURE (2+2)CYCLOADDITION OF TOLUENE-4-SULPHONYL ISOCYANATE TO GLYCALS
Chmielewski, Marek,Kakuza, Zbigniew,Bekzecki, Czeslaw,Sakanski, Piotr,Jurczak, Janusz,Adamowicz, Halina
, p. 2441 - 2450 (2007/10/02)
High-pressure (2+2)cycloaddition of toluene-4-sulphonyl isocyanate to glycals is examined.Reactions proceed regiospecifically to afford single products in case of all 3-substituted glycals.Upon heating or even after standing at room temperature adducts undergo retro-addition to give starting glycals.Various aspects of the cycloaddition are discussed, especially retro-reaction and rearrangement of β-lactams to α,β-unsaturated amides.
THE SYNTHESIS OF OPTICALLY PURE β-LACTAMS DERIVED FROM SUGARS. HIGH-PRESSURE CYCLOADDITION OF TOLUENE-4-SULPHONYL ISOCYANATE TO GLYCALS.
Chmielewski, M.,Kaluza, Z.,Belzecki, C.,Salanski, P.,Jurczak, J.
, p. 4797 - 4800 (2007/10/02)
Cycloaddition of toluene-4-sulphonyl isocyanate to glycals 1-4 at room temperature under 10 kbar pressure gave respective β-lactams 5-8 in good yields.The reaction proceeds regio- and stereospecifically to afford the four-membered ring in position trans to the acetoxy group at C-3 of the glycal moiety.
