Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines

Yuta Kondo, Tetsuya Kadota, Yoshinobu Hirazawa, Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima

研究成果: ジャーナルへの寄稿記事

抄録

N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.

元の言語英語
ページ(範囲)120-125
ページ数6
ジャーナルOrganic Letters
22
発行部数1
DOI
出版物ステータス出版済み - 1 3 2020

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Scandium
scandium
nitrogen compounds
synthesis
glycine
ketones
imines
reagents
isolation
Nitrogen Compounds
catalysts
Lewis Acids
acids
Schiff Bases
Ketones
Glycine
Functional groups
Nitrogen
Catalysts
ketimine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines. / Kondo, Yuta; Kadota, Tetsuya; Hirazawa, Yoshinobu; Morisaki, Kazuhiro; Morimoto, Hiroyuki; Ohshima, Takashi.

:: Organic Letters, 巻 22, 番号 1, 03.01.2020, p. 120-125.

研究成果: ジャーナルへの寄稿記事

Kondo, Yuta ; Kadota, Tetsuya ; Hirazawa, Yoshinobu ; Morisaki, Kazuhiro ; Morimoto, Hiroyuki ; Ohshima, Takashi. / Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines. :: Organic Letters. 2020 ; 巻 22, 番号 1. pp. 120-125.
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