We recently reported a tandem dealkoxycarbonylation-Michael addition-based ring expansion sequence (1~ 3) for the preparation of 2, 2-dialkyl-3-oxocyclohexaneacetic esters. L2 The current study sought to extend this methodology 3'4 to the preparation of heterocyclic systems by applying this reaction tandem to readily accessible esters and amides related to 4. We present here our results on the use of the dealkoxycarhonylation- ...