Synthesis

Ring closing metathesis in the synthesis of sultones and sultams

S Karsch, D Freitag, P Schwab, P Metz

Index: Karsch, Sandra; Freitag, Dirk; Schwab, Pia; Metz, Peter Synthesis, 2004 , # 10 p. 1696 - 1712

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Citation Number: 33

Abstract

Abstract Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis (RCM) of sulfonates. The resulting α, β-unsaturated sultones act as dienophiles in intermolecular Diels-Alder reactions. A first cyclic sulfate formation through RCM has been discovered, and a rapid access to β-lactams fused to a sultam moiety of variable ring size was developed from inexpensive, commercially ...