α-Azido ketones, Part 6. Reduction of acyclic and cyclic α-azido ketones into α-amino ketones: Old problems and new solutions

Tamás Patonay, Károly Micskei, Éva Juhász-Tóth, Szabolcs Fekete, Veronika Cs Pardi-Tóth

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Comparative experiments on the selective reduction of α-azido ketones to α-amino ketones revealed that tin(II) chloride reduction followed by immediate protection with Boc group is the method of choice. This methodology proved to be useful for more complex substrates, too. Chromium(II) acetate also resulted in the desired products but in lower yields due to a competitive deazidation procedure. A mechanism to explain this deazidation was suggested.

Original languageEnglish
Pages (from-to)270-290
Number of pages21
JournalArkivoc
Volume2009
Issue number6
DOIs
Publication statusPublished - May 1 2009

Keywords

  • ?-azido ketones
  • Chromium(ii)
  • Selective reduction
  • Tin(ii)
  • α-amino ketones

ASJC Scopus subject areas

  • Organic Chemistry

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