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Starting from readily available  o ‐diazoacyl‐substituted arene carboxylates, scaffolds with the 5,9‐epoxycyclohepta[b]pyran‐2(3 H )‐one core were obtained by cooperative Rh II , Lewis and Brønsted acid catalysis. Four new bonds, three functional groups (lactone, ketal, and alcohol) and four contiguous stereocenters are formed during this regio‐ and diastereoselective process in a single synthetic step. Intensive optimization and mechanistic studies, including the trapping, isolation, and elucidation of reaction intermediates, led to a plausible mechanistic scenario. The reaction is proposed to involve carbonyl ylides but also transient species of the ketocarbene equilibrium that undergo a cascade of cycloaddition and skeletal rearrangements.

chemistry – a european journal

Regio‐ and Diastereoselective Dimerization of Diazo Carbonyls: A Cooperative Catalytic Approach to Complex Scaffolds with Four Contiguous Stereocenters