Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide

Keisuke Yoshida, Hina Suzuki, Hiroki Inoue, Kohei Matsui, Yuta Fujino, Yohei Kanoko, Yukihiro Itatsu, Kenichi Takao

Research output: Contribution to journalArticle

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The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as (tert-butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph3SiCl) was developed. The reaction was effectively catalyzed with 4-methoxypyridine N-oxide in the presence of sodium sulfate (Na2SO4). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol. (Figure presented.) .

Original languageEnglish
Pages (from-to)1886-1891
Number of pages6
JournalAdvanced Synthesis and Catalysis
Issue number12
Publication statusPublished - 2016



  • amine N-oxides
  • organocatalysis
  • regioselectivity
  • silicon

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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