Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride.

Abstract

The reaction between cyclopropenones and water catalyzed by different phosphines has been thoroughly investigated. Under the catalysis of trimethylphosphine, highly functionalized γ-butenolides were successfully synthesized from the simple starting material, cyclopropenones, and water in 35%-81% yields with excellent diastereoselectivities. Under the catalysis of triphenylphosphine, cyclopropenones were transferred to trisubstituted α,β-unsaturated acids with sufficient water in 78%-99% yields, while α,β-unsaturated acid anhydrides were obtained with trace water.