Tandem inter [4+2]/intra [3+2] cycloadditions of nitroalkenes. Application to the synthesis of aminocarbasugars

Scott E. Denmark, Martin Juhl

Research output: Contribution to journalArticle

Abstract

The tandem inter [4+2]/intra [3+2] cycloaddition of nitroalkenes in the bridged mode was applied to the stereoselective synthesis of β-D-4-amino-2,4-dideoxycarbagulose, a representative aminocarbasugar. The synthesis required only five steps from known materials and delivered the protected aminocarbasugar (-)-20 in excellent yield (see Scheme 9). The success of the synthetic sequence relies on 1) the ability to incorporate O-substituents at the nitroalkene moiety, 2) the identification of a suitably modified chiral dienophile, and in particular 3) the development of specific experimental conditions and protocols that allow for the formation and isolation of the highly sensitive nitroso acetals. The reduction of the C(1) carbonyl group of (+)-19 gave unexpected stereoselectivity, which could be rationalized by a conformational inversion of the substrate (see Scheme 11).

Original languageEnglish (US)
Pages (from-to)3712-3736
Number of pages25
JournalHelvetica Chimica Acta
Volume85
Issue number11
DOIs
StatePublished - Jan 1 2002

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ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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