Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster

Takashi Ohshima, Takanori Iwasaki, Yusuke Maegawa, Asako Yoshiyama, Kazushi Mashima

Research output: Contribution to journalArticle

128 Citations (Scopus)

Abstract

Acylation of alcohols and amines is one of the most fundamental reactions. Due to the greater nucleophilicity of the amino group compared to the hydroxyl group, complete N-acylation occurs. Only an enzymatic reaction can promote a highly selective O-acylation reaction, and there are no examples using an artificial catalyst. Here we report that the tetranuclear zinc cluster Zn4(OCOCF3)6O efficiently catalyzes highly chemoselective O-acylation in the presence of primary and secondary alkyl amines. Our results suggest the high potential of the zinc cluster as the core structure of an artificial enzyme to realize further enzyme-like chemoselective reactions.

Original languageEnglish
Pages (from-to)2944-2945
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number10
DOIs
Publication statusPublished - Mar 12 2008
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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