Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system

Zsuzsanna Sánta, Pál Kolonits, József Nagy, József Nyitrai

Research output: Contribution to journalArticle

Abstract

In order to distinguish primary and secondary hydroxyl groups in the presence of a β-lactam moiety benzylidene acetal protection and reductive cleavage were used. When the reductive ring opening was carried out using diisobutylaluminium hydride, the benzylidene acetal group remained intact, while the β-lactam was reduced to the corresponding β-amino alcohol. The acetal cleavage with sodium cyanoborohydride was successful, resulting mainly in a β-lactam compound bearing the benzyloxy group on the secondary carbon atom.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalArkivoc
Volume2008
Issue number3
Publication statusPublished - 2008

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Keywords

  • Benzylidene acetal
  • Protecting group
  • Reductive cleavage
  • β-Lactam

ASJC Scopus subject areas

  • Organic Chemistry

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