The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid

VK Aggarwal*, S Roseblade, Rikki Alexander

*Corresponding author for this work

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

51 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis-of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.

Original languageEnglish
Pages (from-to)684-691
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number4
DOIs
Publication statusPublished - 21 Feb 2003

Keywords

  • DIELS-ALDER REACTIONS
  • PHYSICOCHEMICAL PROPERTIES
  • N-OXIDE
  • CISPENTACIN
  • FR109615
  • 2-ALKYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES
  • INTERMEDIATE
  • NITROALKENES
  • 1,3-DIOXIDE
  • EQUIVALENTS

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