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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Crystallographic data (excluding structure factors) for the structure 11 reported in this paper have been deposited with the Cambridge Crystallographic Data
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