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Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework

  作者 AHMAR MOHAMMED; THOME STEPHANE; CAZES BERNARD  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-36;  页码  7093-7105  
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[摘要]Thanks to their lack of polarity, the exocyclic double bonds of 4-alkylidenecyclopentenones 4 are selectively epoxidized by MCPBA to give spiroepoxycyclopentenones 7, which feature the nonclassical 1-oxaspiro[2.4]hept-6-en-5-one framework. Under acidic conditions, compounds 7 undergo ring-opening to afford 4-hydroxy-4-(1-hydroxyalkyl)cyclopentenones 10.

 
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