A convenient synthesis of γ-functionalized cyclopentenones

• Nour Lahmar,
• Taïcir Ben Ayed,
• Moncef Bellassoued and
• Hassen Amri

Beilstein J. Org. Chem. 2005, 1, No. 11, doi:10.1186/1860-5397-1-11

• conjugate addition of nitroalkanes to α,β-unsaturated ketones 1 leading to the nitroalkanes derivatives 2 which may be converted into their γ-diketone homologues 3 using Nef reaction. The intramolecular cyclization of 1,4-diketones 3 led to the corresponding cyclopentenones 4. Results and discussion As

• C9H14O4: 186.0892. Found: 186.0877. Preparation of γ-functionalized cyclopentenones (4): General procedure To a solution of 1,4-diketone 3 (5 mmol) in MeOH (10 mL) was added 1 equivalent of K2CO3, the mixture was bring to reflux during one hour. After workup, the product 4 was purified by column