THE SYNTHESIS OF OPTICALLY PURE β-LACTAMS DERIVED FROM SUGARS. HIGH-PRESSURE CYCLOADDITION OF TOLUENE-4-SULPHONYL ISOCYANATE TO GLYCALS.

Article abstract of DOI:10.1016/S0040-4039(01)81523-9

<2+2> 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.