The synthesis of optically pure β-lactams derived from sugars. High-pressure [2+2] cycloaddition of toluene-4-sulphonyl isocyanate to glycals. |
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Authors: | M Chmielewski Z Kałuz·a C Bełz·ecki P Sałański J Jurczak |
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Institution: | Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland |
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Abstract: | 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. |
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