Acceleration effect of mild organocatalytic system 2,2′-biphenol/B(OH)3 for 2-aza-Cope rearrangement

Kenji Sugimoto*, Ryoga Yoshida, Yuji Matsuya

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Organocatalysis by the combination of weak acids, namely, 2,2′-biphenol and B(OH)3, for 2-aza-Cope rearrangement is described. Aldehydes and 1,1-diphenyl homoallylamine were converted into the corresponding homoallylamines in moderate-to-high yield in the presence of 10 mol% 2,2′-biphenol and 30 mol% B(OH)3. In contrast to the conventional 2-aza-Cope rearrangement catalyzed by strong activators, a user- and environment-friendly organocatalytic system was established using a combination of inexpensive, easy-to-handle, non-hazardous, and bench-stable reagents.

Original languageEnglish
Article number153922
JournalTetrahedron Letters
Volume102
DOIs
StatePublished - 2022/07/20

Keywords

  • 2,2′-biphenol
  • 2-aza-Cope rearrangement
  • Boric acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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