Ring Closing Metathesis in the Synthesis of Sultones and Sultams

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 available starting materials using RCM as the key operation. An efficient RCM of 4-vinyl-azetidin-2-ones to give 1-aza-bicyclo[4.2.0]oct-4-en-8-ones is also described.

Key words

catalysis - ring closing metathesis - sultones - sultams - beta lactams

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1

X-Ray diffraction analysis.

29

Crystallographic data (excluding structure factors) for the structure 11 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-226916. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax:[phone]; email: [e-mail]).