Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

Tomoya Miura, Takamasa Tanaka, Qiang Zhao, Scott G. Stewart, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.

Original languageEnglish
JournalHelvetica Chimica Acta
Volume100
Issue number2
DOIs
Publication statusPublished - Feb 2017
Externally publishedYes

Keywords

  • 2-Amino ketones
  • Carbenoids
  • Rhodium
  • Sigmatropic rearrangements
  • Triazoles

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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