Aminoketyl Radicals in Organic Synthesis

Stereoselective Cyclization of Five- and Six-Membered Cyclic Imides to 2-Azabicycles Using SmI2-H2O

Shicheng Shi, Michal Szostak

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Synthetic application of aminoketyl radicals [R-C(O-)NR′R″] formed by a direct electron capture into the amide bond is limited. Herein, we demonstrate addition of aminoketyl radicals to unactivated alkenes using SmI2-H2O as a crucial promoter based on the generic five- and six-membered imide template. Notably, this method enables direct access to aminoketyl radicals with wide-ranging applications in synthesis for the formation of C-C bonds adjacent to nitrogen via polarity reversal.

Original languageEnglish (US)
Pages (from-to)5144-5147
Number of pages4
JournalOrganic Letters
Volume17
Issue number20
DOIs
StatePublished - Oct 16 2015

Fingerprint

Imides
Synthetic Chemistry Techniques
Cyclization
imides
Alkenes
Amides
Nitrogen
Electrons
synthesis
electron capture
amides
alkenes
polarity
templates
nitrogen

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Aminoketyl Radicals in Organic Synthesis : Stereoselective Cyclization of Five- and Six-Membered Cyclic Imides to 2-Azabicycles Using SmI2-H2O. / Shi, Shicheng; Szostak, Michal.

In: Organic Letters, Vol. 17, No. 20, 16.10.2015, p. 5144-5147.

Research output: Contribution to journalArticle

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AU - Szostak, Michal

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