Synthesis of conformationally constrained, orthogonally protected 3-azabicyclo[3.2.1]octane β-amino esters

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14 Citations (Scopus)

Abstract

Novel azabicyclic β-amino acid derivatives were readily prepared from diexo or diendo norbornene β-amino acids. The 3-azabicyclo[3.2.1]octane skeleton was obtained by NaIO4-mediated cleavage of the dihydroxylated β-amino ester intermediates, followed by reductive amination. Lipase-catalyzed enantioselective ring opening of racemic exo-norbornene β-lactam allowed preparation of the corresponding azabicyclic exo β-amino acid in enantiopure form.

Original languageEnglish
Pages (from-to)31-39
Number of pages9
JournalArkivoc
Volume2010
Issue number9
DOIs
Publication statusPublished - Jun 16 2010

Keywords

  • Dihydroxylation
  • Enzymatic resolution
  • Ring closure
  • Ring opening
  • β-amino acids

ASJC Scopus subject areas

  • Organic Chemistry

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