Reaction modes of oxidative dimerization of epoxycyclohexenols

Mitsuru Shoji, Satoshi Kishida, Yusuke Kodera, Isamu Shiina, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.

Original languageEnglish
Pages (from-to)7205-7207
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number38
DOIs
Publication statusPublished - 2003 Sep 15
Externally publishedYes

Fingerprint

Dimerization
Epoxy Compounds
Cycloaddition Reaction
Hydrogen Bonding
Hydrogen bonds
Oxidation

Keywords

  • 6π-electrocylization
  • Diels-Alder reaction
  • Epoxyquinol
  • Hydrogen-bonding

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Shoji, M., Kishida, S., Kodera, Y., Shiina, I., Kakeya, H., Osada, H., & Hayashi, Y. (2003). Reaction modes of oxidative dimerization of epoxycyclohexenols. Tetrahedron Letters, 44(38), 7205-7207. https://doi.org/10.1016/S0040-4039(03)01781-7

Reaction modes of oxidative dimerization of epoxycyclohexenols. / Shoji, Mitsuru; Kishida, Satoshi; Kodera, Yusuke; Shiina, Isamu; Kakeya, Hideaki; Osada, Hiroyuki; Hayashi, Yujiro.

In: Tetrahedron Letters, Vol. 44, No. 38, 15.09.2003, p. 7205-7207.

Research output: Contribution to journalArticle

Shoji, M, Kishida, S, Kodera, Y, Shiina, I, Kakeya, H, Osada, H & Hayashi, Y 2003, 'Reaction modes of oxidative dimerization of epoxycyclohexenols', Tetrahedron Letters, vol. 44, no. 38, pp. 7205-7207. https://doi.org/10.1016/S0040-4039(03)01781-7
Shoji M, Kishida S, Kodera Y, Shiina I, Kakeya H, Osada H et al. Reaction modes of oxidative dimerization of epoxycyclohexenols. Tetrahedron Letters. 2003 Sep 15;44(38):7205-7207. https://doi.org/10.1016/S0040-4039(03)01781-7
Shoji, Mitsuru ; Kishida, Satoshi ; Kodera, Yusuke ; Shiina, Isamu ; Kakeya, Hideaki ; Osada, Hiroyuki ; Hayashi, Yujiro. / Reaction modes of oxidative dimerization of epoxycyclohexenols. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 38. pp. 7205-7207.
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