Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

Dániel Fegyverneki, Natália Kolozsvári, Dániel Molnár, Orsolya Egyed, Tamás Holczbauer, Tibor Soós

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2 Citations (Scopus)

Abstract

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

Original languageEnglish
Pages (from-to)2179-2183
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number9
DOIs
Publication statusPublished - Feb 11 2019

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Keywords

  • Ireland–Claisen
  • boranes
  • diastereoselectivity
  • sigmatropic rearrangement
  • silanes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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