Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

Steven Gunawan, Nathan Bedard, Christopher Foley, Christopher Hulme

Research output: Contribution to journalArticlepeer-review

Abstract

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

Original languageEnglish (US)
Article number152978
JournalTetrahedron Letters
Volume69
DOIs
StatePublished - Apr 13 2021

Keywords

  • Bromination
  • CH-functionalization
  • Hypervalent iodine
  • N-acyliminium
  • N-bromosuccinimide
  • Radical

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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