Novel Oxidative Generation of Ammonium Ylides and the Subsequent Silicon Polonovski Reaction

• Honda Kiyoshi

  Graduate School of Engineering, Yokohama National University

• Shibuya Hiromasa

  Graduate School of Engineering, Yokohama National University

• Hoshino Yujiro

  Graduate School of Environment and Information Sciences, Yokohama National University

• Inoue Seiichi

  Graduate School of Environment and Information Sciences, Yokohama National University

Abstract

We have demonstrated a novel oxidative generation of ammonium ylides by employing allylic amines having a silyl group. Treatment of N-(α-silylmethyl)-N-allylic amines with an oxidant, followed by acetic anhydride, brought about a tandem Brook rearrangement/silicon Polonovski reaction via the generation of ammonium ylides to give the corresponding amides, whereas the reaction of N-(α-cyano-α-silylmethyl)-N-allylic amines with an oxidant afforded the corresponding formamides.

Journal

• Chemistry Letters

  Chemistry Letters 37 (4), 442-443, 2008

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390282679562261248
• NII Article ID: 10021079662
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2008.442
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/37/4/442/55596918/cl.2008.442.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed