Synthesis of tert -Butyl 1,3-Diaryl-3-oxopropylcarbamates by a regiocontrolled reduction of ketoaziridines

Heshmat A. Samimi, Bohari Mohd. Yamin, Fatemeh Saberi

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc)2O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

Original languageEnglish
Pages (from-to)129-133
Number of pages5
JournalSynthesis (Germany)
Volume47
Issue number1
DOIs
Publication statusPublished - 2015

Fingerprint

Sodium Iodide
Nickel
Chlorides
Crystal structure
Sodium
X rays
bis(tert-butoxycarbonyl)oxide

Keywords

  • aziridines
  • nickel(II) chloride
  • reduction
  • regioselectivity
  • ring opening

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Synthesis of tert -Butyl 1,3-Diaryl-3-oxopropylcarbamates by a regiocontrolled reduction of ketoaziridines. / Samimi, Heshmat A.; Mohd. Yamin, Bohari; Saberi, Fatemeh.

In: Synthesis (Germany), Vol. 47, No. 1, 2015, p. 129-133.

Research output: Contribution to journalArticle

Samimi, Heshmat A. ; Mohd. Yamin, Bohari ; Saberi, Fatemeh. / Synthesis of tert -Butyl 1,3-Diaryl-3-oxopropylcarbamates by a regiocontrolled reduction of ketoaziridines. In: Synthesis (Germany). 2015 ; Vol. 47, No. 1. pp. 129-133.
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AB - A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc)2O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

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