1,4-Dioxane → 2-[cis-2-(4-Fluoro-phenyl)cyclopropyl]-isoindole-1,3-dione

Participants

Reaction Steps

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (1.57 g, 5 mmol), N-vinyl-phthalimide (2.59 g, 15 mmol), benzyltriethylammonium chloride (114 mg, 0.5 mmol), and rhodium acetate dimer (22 mg, 0.05 mmol) were stirred with dioxane (23 ml) to give a thick slurry. This was stirred overnight at room temperature. TIc (20% EtOAc/hexane) showed good conversion, so the mixture was shaken between EtOAc and water. The organic phase was dried with MgSO4 and evaporated to yield 3.8 g of a crude mixture. This was chromatographed on silica with EtOAc/hexane to yield 169 mg (12%) of 2-[cis-2-(4-fluoro-phenyl)cyclopropyl]-isoindole-1,3-dione

Provenance & Evidence