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

研究成果: Article査読

62 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)17565-17571
ページ数7
ジャーナルChemistry - A European Journal
20
52
DOI
出版ステータスPublished - 2014 12 22

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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