The Reaction of Dimethyl 10-Oxo-3,6-hexanooxepine-4,5-dicarboxylate with Sodium Methoxide/Methanol − A Reinvestigation

Treatment of the bridged oxepine (±)‐1 with a large excess of powdered sodium methoxide in Et2O or with triphenylphosphonium methylide leads to the functionalized hydroazulenes (±)‐2 (69%) and (±)‐3 (81%). Regioselective and stereoselective cyclopropanation of (±)‐2 leads to the dibromocyclopropane derivative (±)‐4. Epoxidation gives the epoxides (±)‐5 and (±)‐6. The resolution of the hydro‐azulenone (±)‐2 is achieved by fractional crystallization of the quinine salt (–)‐8 of the corresponding mono acid (±)‐7. The absolute configuration of (+)‐7 is established by X‐ray analysis of the quinine salt (–)‐8.

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Selective Reactions, Resolution and Absolute Configuration of Bridged Hydroazulenes

Tochtermann¹,

Panitzsch

Petroll

et al. 1998

Eur. J. Org. Chem.

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The Reaction of Dimethyl 10-Oxo-3,6-hexanooxepine-4,5-dicarboxylate with Sodium Methoxide/Methanol − A Reinvestigation

Abstract: Treatment of the title compound 1 with sodium methoxide in ether in the presence of methanol leads to the bicyclopentyl derivative 3. The structure of 3 was established by X‐ray analysis. The structure 2 proposed earlier has to be corrected in favour of 3.

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Selective Reactions, Resolution and Absolute Configuration of Bridged Hydroazulenes

Selective Reactions, Resolution and Absolute Configuration of Bridged Hydroazulenes

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