Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: Asymmetric synthesis of cispentacin

VK Aggarwal*, SJ Roseblade, Juliet K Barrell, Rikki Alexander

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

61 Citations (Scopus)

Abstract

[GRAPHICS]

A highly diastereoselective intramolecular nitrone cycloaddition onto a chiral ketene equivalent, obtained by Horner-Wadsworth-Emmons olefination of either enantiomer of bis-sulfinyl phosphonate 6, is described. Cycloaddition gave 5,5-disubstituted isoxazolidine 10 in good yield as a single diastereomer. Catalytic hydrogenolysis of 10 furnished either enantiomer of optically pure cis-2-aminocyclopentane-1-carboxylic acid.

Original languageEnglish
Pages (from-to)1227-1229
Number of pages3
JournalOrganic Letters
Volume4
Issue number7
DOIs
Publication statusPublished - 4 Apr 2002

Keywords

  • 1,3-DIPOLAR CYCLOADDITION
  • (1R,3R)-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE
  • TRANS-1,3-DITHIANE 1,3-DIOXIDE
  • PHYSICOCHEMICAL PROPERTIES
  • SULFOXIDES
  • OXIDATION
  • FR109615
  • OXAZABOROLIDINES
  • STRATEGY

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