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Synthesis of β-Lactams Bearing Functionalized Side Chains from a Readily Available Precursor

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journal contribution
posted on 20.11.2008, 00:00 by Myung-ryul Lee, Shannon S. Stahl, Samuel H. Gellman
The reaction of chlorosulfonyl isocyanate (CSI) with alkenes provides β-lactams in quantity, and the products have frequently been used for ring-opening polymerization to generate nylon-3 materials. Prior uses of this approach have focused almost entirely on β-lactams with purely hydrocarbon substitutents. We show how a variety of β-lactams bearing protected polar substituents can be generated from CSI-derived building blocks.