Novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group

Teruhiko Ishikawa, Jin Urano, Shushiro Ikeda, Yasuhiro Kobayashi, Seiki Saito

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

"I took the road less traveled by and that has made all the difference." Not only fans of the poet Robert Frost recognize the attraction of the less common reaction path. Rather than the expected [3+2] cycloaddition, a novel ene-like cycloisomerization occurs on deprotonation of allyltrimethylsilyl - oxime compounds when the β-sp2 carbon atom of the allyltrimethylsilyl moiety is tethered to the oxime unit (see scheme). The resulting nitrile oxide functional group serves as an enophile, and the final cyclized product still has two functional groups suitable for further manipulations. TMS = SiMe3.

Original languageEnglish
Pages (from-to)1586-1588
Number of pages3
JournalAngewandte Chemie - International Edition
Volume41
Issue number9
DOIs
Publication statusPublished - May 3 2002

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Nitriles
Oximes
Oxides
Functional groups
Deprotonation
Cycloaddition
Fans
Carbon
Atoms

Keywords

  • Cycloisomerization
  • Nitrile oxides
  • Oximes
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group. / Ishikawa, Teruhiko; Urano, Jin; Ikeda, Shushiro; Kobayashi, Yasuhiro; Saito, Seiki.

In: Angewandte Chemie - International Edition, Vol. 41, No. 9, 03.05.2002, p. 1586-1588.

Research output: Contribution to journalArticle

Ishikawa, Teruhiko ; Urano, Jin ; Ikeda, Shushiro ; Kobayashi, Yasuhiro ; Saito, Seiki. / Novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group. In: Angewandte Chemie - International Edition. 2002 ; Vol. 41, No. 9. pp. 1586-1588.
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