3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo [3.2. 1] octanes

…, A Mouriño, L Castedo, JL Mascareñas

Index: Rumbo, Antonio; Mourino, Antonio; Castedo, Luis; Mascarenas, Jose L. Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6114 - 6120

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Citation Number: 24

Abstract

3-Hydroxy-4-pyridones, which are easily prepared from commercially available 3-hydroxy-4- pyrones, can be readily transformed into 4-methoxy-3-oxidopyridinium ylides by treatment with methyl trifluoromethanesulfonate and subsequent deprotonation with a non- nucleophilic base. These ylides are capable of undergoing cycloaddition to several electron- deficient alkenes, thus allowing the synthesis of highly functionalized azabicyclo [3.2. 1] ...

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