Chemoselective reductive nucleophilic addition to tertiary amides, secondary amides, and N-methoxyamides

Minami Nakajima, Yukiko Oda, Takamasa Wada, Ryo Minamikawa, Kenji Shirokane, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide car-bonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor elec-trophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nu-cleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.

Original languageEnglish
Pages (from-to)17565-17571
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number52
DOIs
Publication statusPublished - 2014 Dec 22

Keywords

  • Amides
  • Chemoselectivity
  • Nitrogen
  • Nucleophilic addition
  • Sequential reactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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