Construction of Oxo-Bridged Diazocines via Rhodium-Catalyzed (4+3) Cycloaddition of Carbonyl Ylides with Azoalkenes

Abstract

Developing efficient strategies for synthesizing novel diazocine compounds is valuable because their use has been limited by their synthetic accessibility. This work describes the catalytic (4+3) cycloaddition reaction of carbonyl ylides with azoalkenes generated in situ. The rhodium-catalyzed cascade reaction features good atom and step economy, providing the first access to oxo-bridged diazocines. The product could be synthesized on a gram scale and converted into diversely substituted dihydroisobenzofurans.

Synthesis of Oxo-Bridged Dibenzoazocines through Ruthenium-Catalyzed [4 + 3]-Cycloannulation of Aza-ortho-quinone Methides with Carbonyl Ylides

“…Subsequently, Schneider described a single synthetic step to furnish oxa-bridged dibenzooxacines with [4 + 3]-cycloannulation of ortho -quinone methides with carbonyl ylides. In 2022, Han et al developed a rhodium-catalyzed [4 + 3] cycloaddition reaction, providing an efficient strategy for constructing oxabicyclic diazocines …”