Synthesis of γ-Aryl Medium-Sized Cyclic Enones by a Domino 4π-Electrocyclic Reaction/Heck–Matsuda Arylation Sequence at Ambient Temperature

Abstract

Bicyclo[n.2.0]cyclobutenes are transformed into medium-sized cyclic γ-aryl enones using a cationic aryl palladium(II) species generated from a diazonium salt. The reaction proceeds at ambient temperature by capturing the cis,trans-cycloalkadiene intermediate generated through a conrotatory 4π-electrocyclic ring opening reaction followed by a Heck–Matsuda arylation sequence. Optically pure γ-aryl enones were also synthesized using point-to-planar-to-point chirality-transfer processes.

Synthesis of polysubstituted fused pyrrolidines via [2 + 2]/[2 + 3] cycloaddition of azomethine ylides

“…In the last two decades, the [2 + 2] cyclization reaction has become a privileged strategy in the synthetic chemists’ toolbox for the synthesis of 3-azabicyclo[3.2.0]heptane backbones. 10 The typical reactions include intramolecular [2 + 2] reactions (Fig. 2a), 11 intermolecular [2 + 2] photocycloadditions (Fig.…”