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Radical Cyclization in Heterocycle Synthesis. Part 10:1A Concise Synthesis of (−)-Kainic Acid via Sulfanyl Radical Addition–Cyclization–Elimination Reaction

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
56
Issue
34
Identifiers
DOI: 10.1016/s0040-4020(00)00579-2
Keywords
  • Kainic Acid
  • Thiophenol
  • Radical Cyclization
  • Pyrrolidine

Abstract

Abstract Sulfanyl radical addition–cyclization–elimination of diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidine in high yield. This reaction was extended to a radical cyclization using a catalytic amount of thiophenol. A successful application was demonstrated by the asymmetric synthesis of (−)-kainic acid.

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