Tetrahedron Letters

Mild conversion of propargylic alcohols to α, β-unsaturated enones in ionic liquids (ILs); a new 'metal free'life for the Rupe rearrangement

GC Nandi, BM Rathman, KK Laali

Index: Nandi, Ganesh C.; Rathman, Benjamin M.; Laali, Kenneth K. Tetrahedron Letters, 2013 , vol. 54, # 46 p. 6258 - 6263

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Citation Number: 10

Abstract

Abstract A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α, β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Brønsted acidic ionic liquid [BMIM-SO 3 H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe→ Aldol ...

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