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

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

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Abstract

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.

Original languageEnglish
Pages (from-to)120-125
Number of pages6
JournalOrganic Letters
Volume22
Issue number1
DOIs
Publication statusPublished - Jan 3 2020

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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