Abstract
Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH 3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26
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